(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

Base Information

Chemical Name:(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid
CAS No.:160912-07-2
Molecular Formula:C₂₃H₂₈O₈
Molecular Weight:432.471
Hs Code.:

Synonyms:(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

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Chemical Property of (1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

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Technology Process of (1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

There total 1 articles about (1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid 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%

: (1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid methyl ester

: 160912-07-2
(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; for 0.666667h; Ambient temperature;
DOI:10.1021/jo00102a025

Reference yield: 69.0%

: 100-39-0
benzyl bromide

: 160912-07-2
(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

: 160912-00-5
Benzyl <1(S)-(1α,3β,4α,5α)>-3,4-bis<<(benzyloxy)methyl>oxy>-1,5-dihydroxycyclohexane-1-carboxylate

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; for 5h; Ambient temperature;
DOI:10.1021/jo00102a025

Reference yield:

: 160912-07-2
(1S,3R,4R,5R)-3,4-Bis-benzyloxymethoxy-1,5-dihydroxy-cyclohexanecarboxylic acid

: <1(R)-(1α,3α,4α,5β)>-3-(Phosphonooxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / Cs₂CO₃ / dimethylformamide / 5 h / Ambient temperature

2: 53 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) -78 deg C, 1 h; 0 deg C, 2 h

3: 100 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 12 h / 2585.7 Torr

With n-butyllithium; hydrogen; caesium carbonate; palladium on activated charcoal; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00102a025