Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate

Base Information

• Chemical Name: Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate
• CAS No.: 1053720-87-8
• Molecular Formula: C₂₉H₅₂O₇Si₂
• Molecular Weight: 568.899
• Mol file: 1053720-87-8.mol

Synonyms:

Chemical Property of Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate

There total 2 articles about Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate 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:

(1S,3R,4R,5S)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanecarboxylic acid methyl ester (1053637-32-3) → Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate (1053720-87-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jo00104a013

Reference yield:

Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate (160911-90-0) → Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate (1053720-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: p-TsOH*H₂O / methanol / 0.5 h / Ambient temperature

With toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00104a013

Reference yield:

Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(hydroxymethyl)cyclohexane-1-carboxylate (1053720-87-8) → Methyl <1(S)-(1α,3β,4α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5,5-bis(hydroxymethyl)cyclohexane-1-carboxylate (1053271-01-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C, 30 min

2: Et₃N / benzene / 4 h / Heating

3: Yb(OTf)3 / tetrahydrofuran; H₂O / Heating

4: NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/jo00104a013

upstream raw materials:

(1S,3R,4R,5S)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate

Downstream raw materials:

(1S,3R,4R,5R)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-formyl-cyclohexanecarboxylic acid methyl ester

Methyl <1(S)-(1α,3β,4α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5,5-bis(hydroxymethyl)cyclohexane-1-carboxylate

(1S,3R,4R,5R)-5-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxymethyl-cyclohexanecarboxylic acid methyl ester