(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

Base Information

• Chemical Name: (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol
• CAS No.: 215370-56-2
• Molecular Formula: C₁₄H₃₀O₅Si
• Molecular Weight: 306.475

Synonyms:(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

Chemical Property of (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

There total 28 articles about (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-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: 90.0%

(3S,4R)-1-hydroxymethyl-3-methoxy-4-(triethylsilyloxy)cyclohex-1-ene (1312696-38-0) → (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol (215370-56-2)

Guidance literature:

(3S,4R)-1-hydroxymethyl-3-methoxy-4-(triethylsilyloxy)cyclohex-1-ene; With osmium(VIII) oxide; trimethylamine-N-oxide; In 2-methyl-propan-1-ol; water; at 20 ℃; for 8h; Inert atmosphere;

With sodium sulfite; In 2-methyl-propan-1-ol; water; at 20 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.03.015

Reference yield: 87.0%

(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol (870862-60-5) → (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol (215370-56-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 0 ℃; for 4h;

DOI:10.1021/jo051686m

Reference yield: 60.0%

(1R,2S,3S,4R)-1,2-Dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexanecarboxylic acid methyl ester (215370-55-1) → (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol (215370-56-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0957-4166(98)00284-5

upstream raw materials:

(1R,2S,3S,4R)-1,2-Dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexanecarboxylic acid methyl ester

(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

(1S,2S,3R,4R)-1-hydroxymethyl-3-methoxycyclohexan-1,2,4-triol

(1R,4S,5S,6R)-4-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-methoxy-2-cyclohexen-1-ol

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester

(-)-ovalicin

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