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

Base Information

• Chemical Name: 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
• CAS No.: 252896-23-4
• Molecular Formula: C₂₇H₃₆O₁₃
• Molecular Weight: 568.575
• Mol file: 252896-23-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 72.0%

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,4aR,8R,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-4-yl ester (252896-22-3) → 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)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm990422n

Reference yield: 68.0%

C27H34O13 → 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)

Guidance literature:

C₂₇H₃₄O₁₃; With sodium cyanoborohydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Molecular sieve;

With hydrogenchloride; sodium carbonate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.166667h;

Reference yield:

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/jm990422n

upstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,4aR,8R,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-4-yl ester

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

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

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

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