(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

Base Information

Chemical Name:(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester
CAS No.:273728-87-3
Molecular Formula:C₃₃H₄₀O₁₈
Molecular Weight:724.67
Hs Code.:

(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

Synonyms:(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

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Chemical Property of (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

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Technology Process of (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

There total 3 articles about (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl 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: 83.0%

: 273728-74-8
Acetic acid (3aR,4R,5R,6R,7aR)-6-acetoxy-1,3-dioxo-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-octahydro-isobenzofuran-5-yl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 273728-87-3
(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 2h;
DOI:10.1016/S0040-4039(00)00225-2

Reference yield:

: 106758-60-5
(1E)-(2',3',4',6'-tetra-O-acetyl-β-D-gucopyranosyloxy)buta-1,3-diene

: 273728-87-3
(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: dimethylsulfoxide / 18 h / 20 °C

1.2: 64 percent / OsO₄; NMO / acetone; H₂O / 0.5 h / -10 °C

2.1: 84 percent / HClO₄ / 2 h

3.1: 83 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h

With dmap; perchloric acid; triethylamine; In dichloromethane; dimethyl sulfoxide; 1.1: Diels-Alder reaction / 1.2: Upjohn dihydroxilation / 2.1: Acetylation / 3.1: alcoholysis;
DOI:10.1016/S0040-4039(00)00225-2

Reference yield:

: 273728-83-9
Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3aR,4R,5R,6R,7aR)-5,6-dihydroxy-1,3-dioxo-octahydro-isobenzofuran-4-yloxy)-tetrahydro-pyran-3-yl ester

: 273728-87-3
(1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / HClO₄ / 2 h

2: 83 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h

With dmap; perchloric acid; triethylamine; In dichloromethane; 1: Acetylation / 2: alcoholysis;
DOI:10.1016/S0040-4039(00)00225-2