1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose

Base Information

• Chemical Name: 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose
• CAS No.: 138857-85-9
• Molecular Formula: C₃₁H₂₈O₁₁
• Molecular Weight: 576.557
• Mol file: 138857-85-9.mol

Synonyms:1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose

Chemical Property of 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose

There total 6 articles about 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose 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: 34.0%

2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride (138857-92-8) + benzyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside (195063-73-1) → 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose (138857-85-9) + (2R,4aR,6R,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-((2R,3R,4S,5R,6R)-3,5-bis-benzoyloxy-2-benzoyloxymethyl-6-benzyloxy-tetrahydro-pyran-4-yloxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Guidance literature:

With 2,4,6-trimethyl-pyridine; 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 0.5h; Yields of byproduct given; Ambient temperature;

DOI:10.1002/prac.19973390196

Reference yield: 29.0%

1,2,3-tri-O-benzoyl-α-D-galactopyranoside (3253-22-3) + methyl pyruvate diphenyl dithioacetal (105961-89-5) → 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose (138857-85-9) + (2S,4aR,6R,7R,8S,8aS)-6,7,8-Tris-benzoyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (138857-86-0)

Guidance literature:

With nitrosonium tetrafluoroborate; In dichloromethane; at -25 ℃; for 4h;

Reference yield:

1,2,4,6-tetra-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside (30572-03-3) → 1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose (138857-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / 30percent HBr / acetic acid; CH₂Cl₂ / 1.5 h / Ambient temperature

2: 69 percent / AgOTf, molecular sieves 3 Angstroem, 2,4,6-trimethylpyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 100 percent / thiourea / methanol; CH₂Cl₂ / 1) r.t., 14 h, 2) 60 deg C, 6 h

4: AgOTf, molecular sieves 3 Angstroem, 2,4,6-trimethylpyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; 3 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; thiourea; In methanol; dichloromethane; acetic acid;

DOI:10.1002/prac.19973390196

upstream raw materials:

1,2,3-tri-O-benzoyl-α-D-galactopyranoside

methyl pyruvate diphenyl dithioacetal

2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

benzyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside

Downstream raw materials:

2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside

methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside