(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane
CAS No.:581060-41-5
Molecular Formula:C₃₃H₄₈O₈SSi
Molecular Weight:632.891
Hs Code.:

Synonyms:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

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Chemical Property of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

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Technology Process of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

There total 13 articles about (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane 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: 100.0%

: 581060-40-4
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

: 581060-41-5
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

Guidance literature:: With Dess-Martin periodane;
DOI:10.1016/S0040-4039(03)01186-9

Reference yield:

: 581060-36-8
(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one

: 581060-41-5
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

Guidance literature:: Multi-step reaction with 7 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

2.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 85 percent / diethyl ether / 0.33 h / -78 °C

3.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

4.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

5.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

6.1: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 - 20 °C

7.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 23 h / 0 - 20 °C

With n-butyllithium; copper(l) cyanide; Dess-Martin periodane; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-33-5
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

: 581060-41-5
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-methoxymethyloxy-3-[(R)-1'-(p-toluenesulfonyloxy)-2'-oxopropyl]-4-vinylcyclohexane

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 85 percent / diethyl ether / 0.33 h / -78 °C

2.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

4.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

5.1: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 - 20 °C

6.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 23 h / 0 - 20 °C

With n-butyllithium; copper(l) cyanide; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1016/j.tet.2006.04.079