Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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-acetoxymethyl-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.: 172147-74-9
• Molecular Formula: C₄₇H₅₈O₁₅
• Molecular Weight: 862.969
• Mol file: 172147-74-9.mol

Synonyms:Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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 of Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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 3 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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: 95.0%

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,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester (172276-07-2) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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 (172147-74-9)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; for 24h;

DOI:10.1016/S0040-4020(96)01178-7

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-acetoxymethyl-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 (172147-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / trimethylsilyl-trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / 1 h

2: 95 percent / tetrabutylammonium bromide, molecular sieves 4 Angstroem, copper(II) bromide / CH₂Cl₂; dimethylformamide / 24 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(96)01178-7

Reference yield:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-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 (172147-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / trimethylsilyl-trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / 1 h

2: 95 percent / tetrabutylammonium bromide, molecular sieves 4 Angstroem, copper(II) bromide / CH₂Cl₂; dimethylformamide / 24 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(96)01178-7

upstream raw materials:

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

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

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

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

Downstream raw materials:

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester

(2S,4aR,6R,7R,8S,8aS)-7-(2-Allyloxy-ethoxy)-8-benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxine

2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethanol