(R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

Base Information

• Chemical Name: (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol
• CAS No.: 126019-72-5
• Molecular Formula: C₃₀H₅₀O₅Si
• Molecular Weight: 518.809
• Mol file: 126019-72-5.mol

Synonyms:(R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

Chemical Property of (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

There total 24 articles about (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol 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:

methyl 1-methyl-2-oxocyclopentane-1-carboxylate (30680-84-3) → (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-72-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) sodium hydride / 1) THF, r.t., 1 h, 2) THF, 15 h

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 24 h / Ambient temperature

3: 57 percent / BH₃*THF / tetrahydrofuran / 20 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

8: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

With 1H-imidazole; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; hydrogen; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00297a024

Reference yield:

methyl 1-methyl-2-oxocyclopentane-1-carboxylate (30680-84-3) → (S)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-72-5,126107-92-4,126107-93-5,126107-96-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) sodium hydride / 1) THF, r.t., 1 h, 2) THF, 15 h

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 24 h / Ambient temperature

3: 57 percent / BH₃*THF / tetrahydrofuran / 20 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

8: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

With 1H-imidazole; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; hydrogen; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00297a024

Reference yield:

methyl (E)-(2-hydroxyethylidene)-1-methylcyclopentanecarboxylate (126019-40-7) → (R)-((R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopent-1-enyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-72-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

4: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

5: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00297a024

upstream raw materials:

1-<(benzyloxy)methyl>-2-bromo-3-(methoxymethoxy)-1-cyclopentene

(1S*,2R*)-2-<2-(tert-butyldimethylsiloxy)-ethyl>-1-methylcyclopentanecarboxaldehyde

3-ethoxycyclopent-2-en-1-one

methyl 1-methyl-2-oxocyclopentane-1-carboxylate

Downstream raw materials:

Dithiocarbonic acid O-((R)-((1S,2S,5R)-2-benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methyl) ester S-methyl ester

(R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

{2-[(1R,2R)-2-((1R,2R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentylmethyl)-2-methyl-cyclopentyl]-ethoxy}-tert-butyl-dimethyl-silane

Dithiocarbonic acid O-((S)-((1S,2S,5R)-2-benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methyl) ester S-methyl ester