2,3-O-Isopropylidene-D-erythronolactone
- CAS No.
- 25581-41-3
- Chemical Name:
- 2,3-O-Isopropylidene-D-erythronolactone
- Synonyms
- 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTOL;2,3-O-Isopropylidene-D-erythronolactone;2,3-O-Isopropylidene-D-erythronolactone>(-)-2,3-O-Isopropylidene-D-erythronolactone;(-)-2,3-O-ISOPROPYLIDENE-D-ERYTHRONO-LACTONE;(-)-2,3-O-Isopropylidene-D-erythronolactone 98%;D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone;(?)-2,3-O-Isopropylidene-
D -erythronolactone;(3aR,6aR)-2,2-Dmethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one;2,3-O-Isopropylidene-D-erythronolactone
- CBNumber:
- CB6412227
- Molecular Formula:
- C7H10O4
- Molecular Weight:
- 158.15
- MDL Number:
- MFCD00134440
- MOL File:
- 25581-41-3.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 67-69 °C(lit.) |
|---|---|
| Boiling point | 259.7±35.0 °C(Predicted) |
| Density | 1+-.0.06 g/cm3(Predicted) |
| refractive index | -117 ° (C=1, H2O) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Chloroform (Slightly), Water (Slightly) |
| form | Powder |
| color | White to Off-white |
| optical activity | [α]20/D 118°, c = 1 in H2O |
| Water Solubility | Soluble in water |
| BRN | 1282952 |
| InChI | 1S/C7H10O4/c1-7(2)10-4-3-9-6(8)5(4)11-7/h4-5H,3H2,1-2H3/t4-,5-/m1/s1 |
| InChIKey | WHPSMBYLYRPVGU-RFZPGFLSSA-N |
| SMILES | CC1(C)O[C@@H]2COC(=O)[C@@H]2O1 |
| CAS DataBase Reference | 25581-41-3(CAS DataBase Reference) |
| UNSPSC Code | 12352201 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| PPE | Eyeshields, Gloves, type N95 (US) |
|---|---|
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| HS Code | 2932.20.5050 |
| Storage Class | 11 - Combustible Solids |
2,3-O-Isopropylidene-D-erythronolactone price More Price(36)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 377090 | (?)-2,3-O-Isopropylidene-D-erythronolactone 98% | 25581-41-3 | 1g | $98.3 | 2026-04-30 | Buy |
| Sigma-Aldrich | 377090 | (?)-2,3-O-Isopropylidene-D-erythronolactone 98% | 25581-41-3 | 5g | $467 | 2026-04-30 | Buy |
| TCI Chemical | I0454 | 2,3-O-Isopropylidene-D-erythronolactone >98.0%(GC) | 25581-41-3 | 1g | $338 | 2026-04-30 | Buy |
| TRC | TRC-I825000-500MG | 2,3-O-Isopropylidene-D-erythronolactone | 25581-41-3 | 500mg | $91 | 2026-06-03 | Buy |
| TRC | TRC-I825000-2.5G | 2,3-O-Isopropylidene-D-erythronolactone | 25581-41-3 | 2.5g | $307 | 2026-06-03 | Buy |
2,3-O-Isopropylidene-D-erythronolactone Chemical Properties, Uses, Production
Uses
As a chiral synthon, 2,3-O-Isopropylidene-D-erythronolactone can be used for the synthesis of certain natural products such as the leukotrienes.
Uses
It undergoes Aldol condensations with silyl ketene acetals.1 Employed in spiroannulated carbohydrate synthesis.2 Convergent syntheses of a hydroxylated indolizidine,3 carbohydrate substituted benzoquinones,4 and of the oxazole segment of calyculin5 have been accomplished using this chiral synthon.
Uses
Undergoes Aldol condensations with silyl ketene acetals. Employed in spiroannulated carbohydrate synthesis. Convergent syntheses of a hydroxylated indolizidine, carbohydrate substituted benzoquinones, and of the oxazole segment of calyculin have been accomplished using this chiral synthon.
Synthesis
77-76-9
15667-21-7
25581-41-3
General procedure for the synthesis of 2,3-O-isopropylidene-D-erythroketonolactone from 2,2-dimethoxypropane and (3R,4R)-3,4-dihydroxydihydrofuran-2(3H)-one: Na2CO3 (42.4 g, 0.400 mol) was added batchwise to aqueous (500) solution of D-isoscorbic acid (35.2 g, 0.200 mol) at 0 °C. mL) solution. Subsequently, H2O2 (31.3% w/w, 44.0 mL, 0.450 mol) was added slowly and dropwise over 30 min. The reaction solution was stirred at 0 °C for 30 min, then warmed up to 40 °C and continued stirring for 1 h. Decolorized charcoal (Norit A, 8.0 g) was added to break down the excess peroxide and stirred until the starch-iodide test was negative (about 30 min). The reaction mixture was filtered through Celite and washed with water. The filtrate was acidified to pH 1 with 6 M HCl and subsequently concentrated under reduced pressure. To the residue was added acetone (175 mL) and MgSO4 (50 g), stirred and then 2,2-dimethoxypropane (350 mL, 2.85 mol) and TsOH-H2O (420 mg, 2.21 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 16 h. Concentrated aqueous NH4OH (20 mL) was added and stirring was continued for 10 min. The reaction mixture was diluted with Et2O (500 mL) and filtered. The filter cake was washed with Et2O (300 mL), the organic phases were combined and concentrated under reduced pressure. The residue was dissolved in Et2O, dried by adding MgSO4 (10 g), filtered through Celite and the filtrate concentrated under reduced pressure. Purification by recrystallization (Et2O/30-40 °C petroleum ether) afforded the target product 2,3-O-isopropylidene-D-erythroketonolactone (13.5 g, 43%, >99:1 dr) as a light yellow solid. [α]25D = -113 (c 1.0 in H2O); literature value [α]25D = -120 (c 1.0 in H2O); melting point 55-58 °C; literature value melting point 64-65 °C; 1H NMR (400 MHz, CDCl3) δ 1.41 (3H, s, MeCMe), 1.49 (3H, s, MeCMe), 4.39- 4.50 (2H, m, C(5)H2), 4.76 (1H, d, J=5.7 Hz, C(3)H), 4.89 (1H, dd, J=5.7,3.8 Hz, C(4)H).
References
[1] Journal of Organic Chemistry, 2000, vol. 65, # 11, p. 3432 - 3442
[2] Tetrahedron Letters, 1980, vol. 21, # 43, p. 4163 - 4166
[3] Journal of the American Chemical Society, 1983, vol. 105, # 11, p. 3661 - 3672
[4] Organic and Biomolecular Chemistry, 2005, vol. 3, # 9, p. 1795 - 1800
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 13, p. 3427 - 3437
2,3-O-Isopropylidene-D-erythronolactone Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Meryer (Shanghai) Chemical Technology Co., Ltd. | 4006356688 18621169109 | market03@meryer.com | China | 40202 | 62 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Energy Chemical | 400-0056266 | sales8178@energy-chemical.com | China | 44850 | 61 |
| Capot Chemical Co., Ltd | +86 (0) 571 85 58 67 18 | China | 18187 | 66 | |
| Shanghai Longsheng chemical Co.,Ltd. | 58099637 13585536065 | sales@shlschem.com | China | 9880 | 59 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
| Chemsky (shanghai) International Co.,Ltd | 021-50135380 | shchemsky@sina.com | China | 15350 | 60 |
| Maya High Purity Chemicals | +86 (573) 82222445 (0)18006601000 452520369 | sales@maya-r.com | China | 11693 | 57 |
View Latest Price from 2,3-O-Isopropylidene-D-erythronolactone manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-17 | 2,3-O-Isopropylidene-D-erythronolactone
25581-41-3
|
10G | 98%min | 30kg/month | WUHAN FORTUNA CHEMICAL CO., LTD | ||
 |
2019-07-06 | 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
25581-41-3
|
$1.00 | 1kg | 98% | 100KG | Career Henan Chemical Co |
-
- 2,3-O-Isopropylidene-D-erythronolactone
25581-41-3
- $0.00
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
25581-41-3
- $1.00
- 98%
- Career Henan Chemical Co
