(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester
CAS No.:848842-35-3
Molecular Formula:C₂₉H₃₄O₉
Molecular Weight:526.584
Hs Code.:

(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

Synonyms:(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

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Chemical Property of (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

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Technology Process of (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

There total 5 articles about (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

: 848842-30-8
methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

: 96150-84-4
(3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

: 848842-35-3
(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

: 848842-28-4
methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside

: 848842-35-3
(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / diethyl ether; hexane / 1 h / 20 °C

1.2: 50 percent / diethyl ether; hexane / 1 h

2.1: 72 percent / 4-toluenesulfonic acid / palladium/charcoal / methanol / Heating

3.1: 70 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; n-butyllithium; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; 1.2: Wittig reaction;
DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

: 848842-27-3
methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside

: 848842-35-3
(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 68 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 6.5 h / -40 - 20 °C

2.1: n-butyllithium / diethyl ether; hexane / 1 h / 20 °C

2.2: 50 percent / diethyl ether; hexane / 1 h

3.1: 72 percent / 4-toluenesulfonic acid / palladium/charcoal / methanol / Heating

4.1: 70 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1016/j.tetasy.2004.12.001