[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

Base Information

Chemical Name:[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
CAS No.:691882-92-5
Molecular Formula:C₅₀H₆₂O₁₀Si
Molecular Weight:851.122
Hs Code.:

[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

Synonyms:[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

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Chemical Property of [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

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Technology Process of [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

There total 8 articles about [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 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: 95.0%

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

: 691882-87-8
[3aR,4R,5S,6aS]-3-hydroxymethylene-5-methyl-4-(2-trimethylsilanylethoxymethoxymethyl)hexahydro-cyclopenta[b]furan-2-one

: 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

Guidance literature:: With potassium carbonate; In 1-methyl-pyrrolidin-2-one; for 4h;
DOI:10.1021/ja0493796

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield:

: 371778-63-1
acetic acid 2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-ylmethyl ester

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: CuBr*Me₂S / diethyl ether; tetrahydrofuran / 3 h / -45 °C

1.2: 85 percent / p-TsOH / diethyl ether / 8 h

2.1: aq. NaOH / ethanol / Heating

2.2: CO₂ / H₂O

3.1: KI; I₂ / H₂O / 0 °C

4.1: 45 mg / Raney(R)-Ni; EtOH / CH₂Cl₂ / 1 h / 20 °C

5.1: 97 percent / Bu₄NF; i-PrNEt / CH₂Cl₂ / 3 h / 20 °C

6.1: NaH / diethyl ether / 0.08 h / 20 °C

6.2: 96 percent / diethyl ether / 20 h

7.1: 95 percent / K₂CO₃ / 1-methyl-pyrrolidin-2-one / 4 h

With sodium hydroxide; copper(I) bromide dimethylsulfide complex; ethanol; i-PrNEt; Raney(R)-Ni; tetrabutyl ammonium fluoride; iodine; sodium hydride; potassium carbonate; potassium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; ethanol; dichloromethane; water; 1.1: Curran reaction;
DOI:10.1021/ja0493796