(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol

Base Information

• Chemical Name: (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol
• CAS No.: 334670-40-5
• Molecular Formula: C₄₁H₄₆O₆Si
• Molecular Weight: 662.898

Synonyms:(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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

There total 5 articles about (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]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: 92.0%

(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol (334670-39-2) → (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol (334670-40-5)

Guidance literature:

With dimethylaluminum chloride; In hexane; dichloromethane; at -25 - 20 ℃; for 2h;

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

Reference yield:

(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)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol (334670-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KN(SiMe₃)2 / tetrahydrofuran; toluene / 0.17 h / -80 °C

1.2: 70 percent / tetrahydrofuran; toluene / 1 h / -80 - 20 °C

2.1: 88 percent / NH₄F / methanol; tetrahydrofuran / 2 h / Heating

3.1: 97 percent / pyridine / 0.33 h / 20 °C

4.1: 92 percent / (CH₃)2AlCl / CH₂Cl₂; hexane / 2 h / -25 - 20 °C

With pyridine; ammonium fluoride; dimethylaluminum chloride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 1.2: Wittig reaction;

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

Reference yield:

(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane (213777-18-5) → (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol (334670-40-5)

Guidance literature:

Multi-step reaction with 5 steps

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

2.1: KN(SiMe₃)2 / tetrahydrofuran; toluene / 0.17 h / -80 °C

2.2: 70 percent / tetrahydrofuran; toluene / 1 h / -80 - 20 °C

3.1: 88 percent / NH₄F / methanol; tetrahydrofuran / 2 h / Heating

4.1: 97 percent / pyridine / 0.33 h / 20 °C

5.1: 92 percent / (CH₃)2AlCl / CH₂Cl₂; hexane / 2 h / -25 - 20 °C

With pyridine; ammonium fluoride; dimethylaluminum chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 2.2: Wittig reaction;

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

upstream raw materials:

(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol

(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

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol

Downstream raw materials:

(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-4-methoxycarbonylbut-2-enyl]cyclopentane-1,4-diol

(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-[(Z)-4-methoxycarbonylbut-2-enyl]-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol

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

(1S,2R,3R,4R)-1,4-di-O-benzoyl-3-[(Z)-4-methoxycarbonylbut-2-enyl]-2-(hydroxymethyl)cyclopentane-1,4-diol

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