(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

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Chemical Name:(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol
CAS No.:1313195-33-3
Molecular Formula:C₂₇H₃₈O₃Si
Molecular Weight:438.682
Hs Code.:

Synonyms:(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

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Chemical Property of (1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

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Technology Process of (1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

There total 6 articles about (1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol 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: 69.0%

: 100-39-0
benzyl bromide

: 338460-85-8
(1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

: 1313195-33-3
(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

Guidance literature:: (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 338460-84-7
(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone

: 1313195-33-3
(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tris(acetoxy)borohydride / acetic acid / 0.5 h

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; In tetrahydrofuran; acetic acid;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 338460-83-6
dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate

: 1313195-33-3
(1S,4S,5R)-4-O-benzyl-5-benzyloxymethyl-1-O-(tert-butyldimethylsilyl)cyclohex-2-en-1,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C

2.1: sodium periodate / tetrahydrofuran; water / 0.5 h

3.1: sodium tris(acetoxy)borohydride / acetic acid / 0.5 h

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With sodium periodate; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; In tetrahydrofuran; water; acetic acid;
DOI:10.1016/j.carres.2011.04.011