[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

Base Information

Chemical Name:[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one
CAS No.:691882-86-7
Molecular Formula:C₄₄H₄₈O₉
Molecular Weight:720.86
Hs Code.:

[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

Synonyms:[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

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Chemical Property of [3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

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Technology Process of [3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

There total 10 articles about [3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one 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: 75.0%

: 691882-92-5
[3E,3aS,4R,5S,6aS]-5-methyl-4-(2-trimethylsilanylethoxymethoxymethyl)-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

: 691882-86-7
[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: With n-butanethiol; magnesium bromide; In diethyl ether; dichloromethane; at 20 ℃; for 7h;
DOI:10.1021/ja0493796

Reference yield:

: 4196-35-4
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide

: 691882-86-7
[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / K₂CO₃ / 1-methyl-pyrrolidin-2-one / 4 h

2: 75 percent / n-BuSH; MgBr₂ / diethyl ether; CH₂Cl₂ / 7 h / 20 °C

With n-butanethiol; potassium carbonate; magnesium bromide; In 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane;
DOI:10.1021/ja0493796

Reference yield:

: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 691882-86-7
[3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl bromide / CH₂Cl₂; dimethylformamide / 0.5 h / 20 °C

2: 95 percent / K₂CO₃ / 1-methyl-pyrrolidin-2-one / 4 h

3: 75 percent / n-BuSH; MgBr₂ / diethyl ether; CH₂Cl₂ / 7 h / 20 °C

With n-butanethiol; Oxalyl bromide; potassium carbonate; magnesium bromide; In 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0493796