methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate

Base Information

• Chemical Name: methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate
• CAS No.: 326599-33-1
• Molecular Formula: C₃₁H₃₈O₆SSi
• Molecular Weight: 566.791

Synonyms:methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate

Chemical Property of methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate

Chemical Property:

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Technology Process of methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate

There total 5 articles about methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate 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: 94.0%

→ methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate (326599-33-1)

Guidance literature:

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate (326599-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 20 °C

2: K₂CO₃ / methanol / 20 °C

3: Et₃N; DMAP / 20 °C

With 1H-imidazole; dmap; potassium carbonate; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200110)2001:20<3779::AID-EJOC3779>3.0.CO;2-Q

Reference yield:

(1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane (326598-94-1) → methyl (1S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate (326599-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 20 °C

2: K₂CO₃ / methanol / 20 °C

3: Et₃N; DMAP / 20 °C

With 1H-imidazole; dmap; potassium carbonate; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200110)2001:20<3779::AID-EJOC3779>3.0.CO;2-Q

upstream raw materials:

p-toluenesulfonyl chloride

Methyl (1R,3R,5S)-3-t-butyldiphenylsilyloxy-5-hydroxy-cyclohexane-carboxylate

tert-butylchlorodiphenylsilane

(1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane

Downstream raw materials:

(1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-[2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

C₂₃H₂₇⁽²⁾HO₂Si

[(1R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-methanol

(2S,3aR,4aR)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]hexane-3a-carbaldehyde

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