(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

Base Information

Chemical Name:(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol
CAS No.:131289-27-5
Molecular Formula:C₃₁H₃₈O₄Si
Molecular Weight:502.726
Hs Code.:

Synonyms:(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

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Chemical Property of (1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

Chemical Property:

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Technology Process of (1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

There total 4 articles about (1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol 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:

: Trifluoro-methanesulfonic acid (1S,2R,3R,4S,5R)-2,3,4-tris-benzyloxy-5-hydroxy-5-trimethylsilanylmethyl-cyclohexyl ester

: (1R,5S,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-3-enol

: 131289-27-5
(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

Guidance literature:: With 1,5-Diazabicyclo[5.4.0]undec-5-ene; In dichloromethane; at 20 ℃; Yield given. Yields of byproduct given;
DOI:10.1016/0008-6215(90)80147-U

Reference yield:

: 85716-45-6
1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon

: 131289-27-5
(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / pyridinium tosylate / CH₂Cl₂ / 15 h / 20 °C

2: 65 percent / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 3 h, 2.) --> 20 deg C, 16 h

3: pyridine / CH₂Cl₂ / 1 h / 20 °C

4: 1,5-diazabicyclo<5.4.0>undec-5-ene / CH₂Cl₂ / 20 °C

With pyridine; pyridinium p-toluenesulfonate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0008-6215(90)80147-U

Reference yield:

: 131289-26-4
(1R)-(1O,2,4,5/1C,3)-2,3,4-tribenzyloxy-1-(trimethylsilylmethyl)cyclohexane-1,5-diol

: 131289-27-5
(1R,4S,5R,6S)-4,5,6-Tris-benzyloxy-1-trimethylsilanylmethyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 1,5-diazabicyclo<5.4.0>undec-5-ene / CH₂Cl₂ / 20 °C

With pyridine; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In dichloromethane;
DOI:10.1016/0008-6215(90)80147-U