1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

Base Information

Chemical Name:1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol
CAS No.:686737-80-4
Molecular Formula:C₂₄H₃₄O₂SSi
Molecular Weight:414.684
Hs Code.:

Synonyms:1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

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Chemical Property of 1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

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Technology Process of 1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

There total 7 articles about 1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol 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:

: 6228-98-4
phenylthioacetylene

: 686737-80-4
1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(II) chloride; silver hexafluoroantimonate / (R)-2,2'-bis(2,2'-picolinate)BINOL / CH₂Cl₂ / 1.5 h / -78 °C

2.1: tetrahydrofuran / 0.17 h / -20 °C

3.1: lutidine / CH₂Cl₂ / 1 h / -10 °C

4.1: LiAlH₄ / diethyl ether / 0.17 h / 0 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / -78 - 20 °C

6.2: tetrahydrofuran; hexane / 1 h / -78 °C

With silver hexafluoroantimonate; lithium aluminium tetrahydride; n-butyllithium; lutidine; Dess-Martin periodane; copper dichloride; 2,2'-bis(picolinoyloxy)-(1R)-1,1'-binaphthalene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja049750p

Reference yield:

: 1112-56-7
tetravinyltin (IV)

: 686737-96-2
(1S,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-ene-1-carbaldehyde

: 686737-80-4
1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

Guidance literature:: tetravinyltin (IV); With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.58333h;

(1S,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-ene-1-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1021/ja049750p

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 686737-80-4
1-((1R,2S,5R)-7-Phenylsulfanyl-2-triethylsilanyloxy-2-vinyl-bicyclo[3.2.0]hept-6-en-1-yl)-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: lutidine / CH₂Cl₂ / 1 h / -10 °C

2.1: LiAlH₄ / diethyl ether / 0.17 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / -78 - 20 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; lutidine; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja049750p