2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether

Base Information

• Chemical Name: 2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether
• CAS No.: 123487-86-5
• Molecular Formula: C₂₄H₄₂O₄SSi₂
• Molecular Weight: 482.832
• Mol file: 123487-86-5.mol

Synonyms:2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether

Chemical Property of 2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether

There total 10 articles about 2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether 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: 75.0%

(1R,3S)-2-[1-Benzenesulfonyl-meth-(Z)-ylidene]-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (123487-97-8,123879-99-2) + tert-butyldimethylsilyl chloride (18162-48-6) → [(2S,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclopent-(Z)-ylidenemethanesulfonyl]-benzene (123487-86-5)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(00)99500-5

Reference yield: 74.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1R,3S)-2-[1-Benzenesulfonyl-meth-(Z)-ylidene]-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (123487-97-8,123879-99-2) → 2-<(Phenylsulfonyl)methylidene>cyclopentane-cis-1,3-diol silyl ether (123487-86-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 72h; Ambient temperature;

DOI:10.1021/ja00201a032

Reference yield:

tris(phenylthio)methane (4832-52-4) → [(2S,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclopent-(Z)-ylidenemethanesulfonyl]-benzene (123487-86-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / SnCl₄ / CH₂Cl₂ / -45 °C

2: 90 percent / DBU / CH₂Cl₂ / 0 °C

3: 75 percent / oxone / methanol; H₂O / Ambient temperature; pH at 5.5 - 6.0 with a borate buffer

4: 94 percent / sodium borohydride, CeCl₃ / methanol / Ambient temperature

5: 64 percent / KOC₄H₉-t / 2-methyl-propan-2-ol / Ambient temperature

6: 60 percent / VO(acac)2, t-C₄H₉OOH / CH₂Cl₂ / Ambient temperature

7: 85 percent / LDA / diethyl ether / 0 °C

8: 75 percent / C₃H₄N₂, DMAP / dimethylformamide / Ambient temperature

With tert.-butylhydroperoxide; dmap; Oxone; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; potassium tert-butylate; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)99500-5

upstream raw materials:

(1R,3S)-2-[1-Benzenesulfonyl-meth-(Z)-ylidene]-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol

tert-butyldimethylsilyl chloride

tris(phenylthio)methane

1-(trimethylsilyloxy)cyclopentene

Downstream raw materials:

(1-rS)-(Phenylsulfonyl)-3-methylene-(6-rR,9-rS)-bis(tert-butyldimethylsiloxy)spiro<4.4>nonane