(3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 94898-37-0
• Molecular Formula: C₂₉H₃₀O₅
• Molecular Weight: 458.554

Synonyms:(3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester

There total 20 articles about (3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester 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: 75.0%

(2R,3S,4S,5S)-dimethyl 2-acetoxy-3,4,5-tribenzyloxy-1,1-cyclohexane dicarboxylate (94898-36-9,96290-94-7,96290-95-8,105368-79-4,108813-40-7,108813-41-8,112709-63-4) → (3S,4S,5S)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarboxylic acid methyl ester (94898-37-0)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; at 110 - 170 ℃;

DOI:10.1246/cl.1984.1919

Reference yield: 66.0%

dimethyl (2R,3R,4R,5S)-2-acetoxy-3,4,5-tris(benzyloxy)cyclohexane-1,1-dicarboxylate (108813-41-8) → methyl (3R,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-carboxylate (94898-37-0,96290-96-9,105368-80-7,108813-42-9)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; at 120 - 170 ℃; for 1h;

DOI:10.1021/jo00386a011

Reference yield: 50.0%

dimethyl (2S,3R,4R,5S)-2-acetoxy-3,4,5-tris(benzyloxy)cyclohexane-1,1-dicarboxylate (108813-40-7) → methyl (3R,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-carboxylate (94898-37-0,96290-96-9,105368-80-7,108813-42-9)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; at 120 - 170 ℃; for 1h;

DOI:10.1021/jo00386a011

upstream raw materials:

dimethyl (2S,3R,4R,5S)-2-acetoxy-3,4,5-tris(benzyloxy)cyclohexane-1,1-dicarboxylate

dimethyl (2R,3R,4R,5S)-2-acetoxy-3,4,5-tris(benzyloxy)cyclohexane-1,1-dicarboxylate

benzyl bromide

2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal

Downstream raw materials:

(3R,4R,5S)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol

DL-(1,2,4/3,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

(1S,2S,3S,4R,5R)-1,2,3,4-tetraacetoxy-5-acetoxymethylcyclohexane

(1S,2S,3S,4R,5R)-pseudo-α-D-glucose

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