(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside
CAS No.:1338920-58-3
Molecular Formula:C₃₉H₄₅NO₁₂S
Molecular Weight:751.852
Hs Code.:

(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

Synonyms:(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

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Chemical Property of (1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

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Technology Process of (1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

There total 4 articles about (1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside 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: 100.0%

: 1338920-56-1
(1R,2R,3R,4R,5R,7R)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

: 1338920-58-3
(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: (1R,2R,3R,4R,5R,7R)-7-benzyloxy-4,5-dihydroxy-5-methoxy-2-methoxycarbonyl-6-oxo-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside; With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at -70 ℃; for 2.33333h;

With citric acid; In dichloromethane; water; stereoselective reaction;
DOI:10.1016/j.tetasy.2011.07.023

Reference yield:

: methyl 7-benzyloxy-4,5-dihydroxy-5-methoxy-6-oxo-4,5-O-diphenylmethylidenebicyclo[2.2.2]oct-2-ene-2-carboxylate

: 1338920-58-3
(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / acetonitrile / 4 h / 20 °C

2.1: methanol; sodium methylate / 3 h / 20 °C

2.2: Serdolit-Red cation-exchange resin

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2.33 h / -70 °C

With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium methylate; triethylamine; In methanol; acetonitrile; 2.1: Zemplen deacetylation;
DOI:10.1016/j.tetasy.2011.07.023

Reference yield:

: 51450-09-0
2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose

: 1338920-58-3
(1S,2R,3R,4R,5S,6R,7R)-7-benzyloxy-4,5,6-trihydroxy-5-methoxy-2-methoxycarbonyl-4,5-O-(diphenylmethylidene)bicyclo[2.2.2]octan-3-yl 2-acetamido-1,2-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / acetonitrile / 4 h / 20 °C

2.1: methanol; sodium methylate / 3 h / 20 °C

2.2: Serdolit-Red cation-exchange resin

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2.33 h / -70 °C

With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium methylate; triethylamine; In methanol; acetonitrile; 2.1: Zemplen deacetylation;
DOI:10.1016/j.tetasy.2011.07.023