ChemicalBook CAS DataBase List 1-5-ANHYDRO-D-MANNITOL CRYSTALLINE

1-5-ANHYDRO-D-MANNITOL CRYSTALLINE synthesis

10synthesis methods

Product Name:1-5-ANHYDRO-D-MANNITOL CRYSTALLINE
CAS Number:492-93-3
Molecular formula:C6H12O5
Molecular Weight:164.16

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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492-93-3
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Yield: 92%

Reaction Conditions:

with pyrographite;copper dichloride;palladium dichloride in methanol at 60; for 8 h;

Steps:

General procedure: To a solution of 1,5-anhydro-2,3,4,6-tetra-O-allyl-Dmannitol(1.0 g, 3.1 mmol) in methanol(70 ml) were addedPdCl2(6.0 mg, 0.031 mmol), activated charcoal (1.0 g), andCuCl2 (0.42 g, 3.1 mmol), the reaction mixture was stirred at60 oC for 8 h. After removing the solid and the solvent, 1,5-anhydro-D-mannitol 6 was obtained in 92% yield (0.47 g):(0.47 g): mp 154-155 oC (lit. [17] 156-157oC); []D20 - 50.5o(c 1, H2O) (lit. [17] []D20 -50.3o (c 1.06, H2O); 1H NMR(D2O): 3.86 (br s, 1H), 3.80 (dd, J = 12.5, 1.5 Hz, 1H), 3.77(dd, J = 12.5, 2.5, Hz, 1H), 3.57 (dd, J = 12.5, 6.4 Hz, 1H),3.55-3.48 (m, 2 H), 3.46 (d, J = 9.5 Hz, 1H), 3.18 (ddd, J =9.5, 6.5, 2.5 Hz, 1H); 13C NMR (D2O): 82.21, 75.20, 71.48,70.69, 68.93, 62.85

References:

Yuan, Changyou;Hollingsworth, Rawle I. [Letters in Organic Chemistry,2013,vol. 10,# 2,p. 77 - 84]

13121-61-4 Synthesis