(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

Base Information

Chemical Name:(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane
CAS No.:334972-61-1
Molecular Formula:C₂₇H₄₂O₄SSi
Molecular Weight:490.78
Hs Code.:

Synonyms:(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

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Chemical Property of (1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

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Technology Process of (1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

There total 15 articles about (1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane 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: 90.0%

: 873-55-2
sodium benzenesulfonate

: 334972-51-9
(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Bromoethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

: 334972-61-1
(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

Guidance literature:: In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)02179-1

Reference yield:

: Methyl 2-{(R)-2'-[(1''S,2''R,5''R)-1''-(tert-butyldimethylsilyloxy)-5''-(1-methylethenyl)-2'-cyclopentyl]tetrahydropyran-5'-ylidene}acetate

: 334972-61-1
(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / 0 °C

2.1: LiBr; s-collidine; DMAP / dimethylformamide / 0.17 h / 0 °C

2.2: 93 percent / Ms₂O / dimethylformamide / 24 h / 4 °C

3.1: 87 percent / dimethylformamide / 16 h / 20 °C

With 2,4,6-trimethyl-pyridine; dmap; diisobutylaluminium hydride; lithium bromide; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/b100777g

Reference yield:

: 350486-10-1
(Z)-2-{(R)-2'-[(1''S,2''R,5''R)-1''-(tert-Butyldimethylsilyloxy)-5''-(1-methylethenyl)-2''-cyclopentyl]tetrahydropyran-5'-ylidene}ethanol

: 334972-61-1
(1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiBr; s-collidine; DMAP / dimethylformamide / 0.17 h / 0 °C

1.2: 93 percent / Ms₂O / dimethylformamide / 24 h / 4 °C

2.1: 87 percent / dimethylformamide / 16 h / 20 °C

With 2,4,6-trimethyl-pyridine; dmap; lithium bromide; In N,N-dimethyl-formamide;
DOI:10.1039/b100777g