(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

Base Information

• Chemical Name: (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol
• CAS No.: 213777-20-9
• Molecular Formula: C₄₅H₇₈O₅Si₃
• Molecular Weight: 783.368
• Mol file: 213777-20-9.mol

Synonyms:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

Chemical Property of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

There total 2 articles about (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)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: 83.0%

(3,3-diisopropoxy-propyl)-triphenyl-phosphonium bromide (72931-54-5) + (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol (213777-19-6) → (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol (213777-20-9)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; -80 deg C; 20 deg C, 2 h;

DOI:10.1016/S0040-4039(98)01290-8

Reference yield:

(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane (213777-18-5) → (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol (213777-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / DIBAL-H / toluene / 0.5 h / -78 °C

2.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

2.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

With sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; toluene; 2.2: Wittig reaction;

DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield: 95.0%

ethanol (64-17-5) + (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol (213777-20-9) → (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol (213777-21-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; for 4h;

DOI:10.1016/S0040-4039(98)01290-8

upstream raw materials:

(3,3-diisopropoxy-propyl)-triphenyl-phosphonium bromide

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

(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane

Downstream raw materials:

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

(1S,2R,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-(hydroxymethyl)cyclopentane-1,4-diol

C₂₆H₂₈O₇

(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-(4-methoxycarbonylbutyl)-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol