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

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 252896-24-5
• Molecular Formula: C₅₄H₆₄O₁₇
• Molecular Weight: 985.092
• Mol file: 252896-24-5.mol

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

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

There total 6 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-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: 78.0%

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester (252896-23-4) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (252896-24-5)

Guidance literature:

With tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 - 200 ℃; for 0.5h; Molecular sieve;

Reference yield:

perbenzyl fucosyl bromide (76946-04-8) + Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester (252896-23-4) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (252896-24-5)

Guidance literature:

With tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 44h;

DOI:10.1021/jm990422n

Reference yield:

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (252896-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NIS; trifluoromethanesulfonic acid / CH₂Cl₂ / 0 °C

2: 72 percent / NaCNBH₃; HCl / diethyl ether; tetrahydrofuran

3: Et₄NBr / dimethylformamide; CH₂Cl₂ / 44 h / 20 °C

With hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; tetraethylammonium bromide; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: reductive ring opening / 3: Condensation;

DOI:10.1021/jm990422n

upstream raw materials:

perbenzyl fucosyl bromide

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

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

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

Downstream raw materials:

2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester

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