Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 172494-08-5
• Molecular Formula: C₅₂H₆₂O₁₄
• Molecular Weight: 911.056

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl 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:

(1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester (172494-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / TBABr, CuBr₂ / dimethylformamide; CH₂Cl₂

2: 75 percent / TMSOTf

With trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)02002-7

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester (172494-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / TBABr, CuBr₂ / dimethylformamide; CH₂Cl₂

2: 75 percent / TMSOTf

With trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)02002-7

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-benzyloxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester (172494-08-5) → (1R,2R)-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cyclohexyl 6-O-benzyl-β-D-galactopyranoside (172494-09-6)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/0040-4039(95)02002-7

upstream raw materials:

(1R,2R)-trans-1,2-cyclohexanediol

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

(1R,2R)-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cyclohexyl 6-O-benzyl-β-D-galactopyranoside

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