(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

Base Information

Chemical Name:(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol
CAS No.:383367-67-7
Molecular Formula:C₂₃H₂₈O₇
Molecular Weight:416.471
Hs Code.:

Synonyms:(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

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Chemical Property of (3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

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Technology Process of (3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

There total 1 articles about (3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 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: 47.0%

: 100-39-0
benzyl bromide

: 29073-91-4,55865-04-8,138196-19-7
1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

: 383367-67-7
(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

Guidance literature:: 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose; With bis(tri-n-butyltin)oxide; In toluene; for 2h; Heating;

benzyl bromide; With tetrabutylammomium bromide; In toluene; for 13h; Further stages.; Heating;
DOI:10.1021/ol016631v

Reference yield: 89.0%

: 123-76-2
levulinic acid

: 383367-67-7
(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

: 383367-64-4
3,6-di-O-benzyl-4-O-levulinate-β-D-mannopyranose-1,2-methyl orthoacetate

Guidance literature:: levulinic acid; With dmap; bis-2-propyl carbonate; In dichloromethane; at 0 ℃; for 0.0833333h;

(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol; With dmap; In dichloromethane; at 20 ℃; for 21h; Further stages.;
DOI:10.1021/ol016631v

Reference yield:

: 383367-67-7
(3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol

: 4-Oxo-pentanoic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIPC; DMAP / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 89 percent / DMAP / CH₂Cl₂ / 21 h / 20 °C

2.1: AcOH / H₂O / 2 h / 20 °C

With dmap; bis-2-propyl carbonate; acetic acid; In dichloromethane; water;
DOI:10.1021/ol016631v