Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Base Information

• Chemical Name: Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside
• CAS No.: 138479-81-9
• Molecular Formula: C₆₀H₅₀O₁₆
• Molecular Weight: 1027.05
• Mol file: 138479-81-9.mol

Synonyms:Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Chemical Property of Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside

There total 7 articles about Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside 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: 61.0%

Benzyl 2,3-di-O-benzoyl-β-D-xylopyranoside (138479-77-3) + 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose (149707-75-5,149707-76-6,138479-78-4) → Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside (138479-81-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In toluene; at -20 ℃; for 1h;

DOI:10.1016/0008-6215(91)89043-F

Reference yield:

2,3,4,6-tetra-O-benzoyl-D-galactose (627466-84-6) → Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside (138479-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / Ambient temperature

2: 85 percent / 4A molecular sieves, trimethylsilyl triflate / toluene / 0.5 h / -20 °C

3: aq. 60percent AcOH / 0.33 h / 100 °C

4: pyridine / 1 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene;

DOI:10.1016/0008-6215(91)89043-F

Reference yield:

Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside (138515-35-2) → Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside (138479-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 4A molecular sieves, trimethylsilyl triflate / toluene / 0.5 h / -20 °C

2: aq. 60percent AcOH / 0.33 h / 100 °C

3: pyridine / 1 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; In toluene;

DOI:10.1016/0008-6215(91)89043-F

upstream raw materials:

benzoyl chloride

benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside

Benzyl 2,3-di-O-benzoyl-β-D-xylopyranoside

2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose

Downstream raw materials:

N-(Benzyloxycarbonyl)-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-L-seryl-glycine benzyl ester

O-<2,3-Di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-N-(9-fluorenylmethoxycarbonyl)-L-seryl-glycine allyl ester

2,3-Di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate

C₆₁H₅₆N₂O₁₉