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

Base Information

• Chemical Name: (1S,3R,4R,5S)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanecarboxylic acid methyl ester
• CAS No.: 1053637-32-3
• Molecular Formula: C₃₅H₆₆O₇Si₃
• Molecular Weight: 683.161
• Mol file: 1053637-32-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1S,3R,4R,5S)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanecarboxylic acid methyl 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:

t-butyldimethylsiyl triflate (69739-34-0) + 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) → (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)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo00104a013

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)>-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 5 steps

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

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

3: Et₃N / benzene / 4 h / Heating

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

5: NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/jo00104a013

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) → (1S,3R,4R,5R)-5-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-formyl-3-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (1055038-65-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: Et₃N / benzene / 4 h / Heating

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

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/jo00104a013

upstream raw materials:

t-butyldimethylsiyl triflate

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:

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

(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