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

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 93661-19-9
• Molecular Formula: C₄₈H₅₄O₁₅
• Molecular Weight: 870.948
• Mol file: 93661-19-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (57783-81-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (93661-19-9)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 45 ℃; for 17h;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside (74801-06-2) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (93661-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / tetrabutylammonium hydrogensulfate, 5 percent sodium hydroxide / CH₂Cl₂ / 10 h / Heating

2: mercuric cyanide / benzene; nitromethane / 17 h / 45 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; mercury(II) cyanide; In nitromethane; dichloromethane; benzene;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (93661-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / tetrabutylammonium hydrogensulfate, 5 percent sodium hydroxide / CH₂Cl₂ / 10 h / Heating

2: mercuric cyanide / benzene; nitromethane / 17 h / 45 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; mercury(II) cyanide; In nitromethane; dichloromethane; benzene;

DOI:10.1016/0008-6215(84)85204-0

upstream raw materials:

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside

benzyl bromide

Downstream raw materials:

(2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

benzyl 2,3,6-tri-O-benzyl-4-O-β-D-glucopyranosyl-β-D-galactopyranoside

benzyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-galactopyranoside

benzyl 4-O-(2-O-allyl-3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside