Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside

Base Information

• Chemical Name: Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside
• CAS No.: 155195-08-7
• Molecular Formula: C₅₃H₇₁FO₁₈Si₂
• Molecular Weight: 1071.31
• Mol file: 155195-08-7.mol

Synonyms:Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside

Chemical Property of Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside

There total 3 articles about Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside 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: 93.0%

Benzyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-mannopyranoside (145259-94-5) + 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose (439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2) → Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside (155195-08-7)

Guidance literature:

boron trifluoride diethyl etherate; In dichloromethane; for 24h; Ambient temperature;

Reference yield: 78.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + Benzyl 2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside (155195-27-0) → Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside (155195-08-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h;

Reference yield:

Benzyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-mannopyranoside (145259-94-5) → Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside (155195-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine-polyhydrogen fluoride / CH₂Cl₂ / 0.08 h / Ambient temperature

2: 78 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -20 °C

With trimethylsilyl trifluoromethanesulfonate; pyridine-polyhydrogen fluoride; In dichloromethane;

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Benzyl 2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside

Benzyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-mannopyranoside

2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose