(1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol

Base Information

• Chemical Name: (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol
• CAS No.: 358395-57-0
• Molecular Formula: C₄₀H₄₄O₇Si
• Molecular Weight: 664.871
• Mol file: 358395-57-0.mol

Synonyms:(1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol

Chemical Property of (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol

There total 9 articles about (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol 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: 72.0%

methyl (5S,7R,8R)-9-(tert-butyldiphenylsilyloxy)-5,7-di(benzoyloxy)-8-iodonon-3(Z)-enoate (358395-63-8) → (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol (358395-57-0)

Guidance literature:

With triethyl borane; oxygen; tri-n-butyl-tin hydride; In xylene; at 20 ℃;

DOI:10.1016/S0040-4039(01)00754-7

Reference yield:

tert-Butyl-[(R)-2-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-iodo-ethoxy]-diphenyl-silane → (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol (358395-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / ZnCl₂ / 0.5 h / -20 °C

2: 88 percent / pyridine / 20 °C

3: 100 percent / HgO; HgCl₂ / acetone; H₂O / Heating

4: 74 percent / KHMDS / tetrahydrofuran / 1 h / -80 - 20 °C

5: Jones reagent / acetone / 2 h / -10 - 20 °C

6: 401 mg / diethyl ether

7: 72 percent / Bu₃SnH; BEt₃; O₂ / p-xylene / 0.67 h / 20 °C

With jones reagent; triethyl borane; oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; mercury dichloride; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; pyridine; diethyl ether; para-xylene; water; acetone;

DOI:10.1016/S0040-4020(03)00258-8

Reference yield:

(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-2,4-di(benzoyloxy)-5-iodohexanal (358395-61-6) → (1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol (358395-57-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / KHMDS / tetrahydrofuran / 1 h / -80 - 20 °C

2: Jones reagent / acetone / 2 h / -10 - 20 °C

3: 401 mg / diethyl ether

4: 72 percent / Bu₃SnH; BEt₃; O₂ / p-xylene / 0.67 h / 20 °C

With jones reagent; triethyl borane; oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; para-xylene; acetone;

DOI:10.1016/S0040-4020(03)00258-8

upstream raw materials:

methyl (5S,7R,8R)-9-(tert-butyldiphenylsilyloxy)-5,7-di(benzoyloxy)-8-iodonon-3(Z)-enoate

benzoyl chloride

(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-1,1-diethylthio-5-iodohexane-2,4-diol

(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-2,4-di(benzoyloxy)-5-iodohexanal

Downstream raw materials:

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane

8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-((E)-3-oxooct-1-enyl)cyclopentane

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(3-oxooctyl)cyclopentane