allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside
• CAS No.: 1260731-83-6
• Molecular Formula: C₄₄H₄₆O₆S
• Molecular Weight: 702.912
• Mol file: 1260731-83-6.mol

Synonyms:allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside

Chemical Property of allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside

There total 1 articles about allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside 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: 70.0%

allyl 3,4,6-tri-O-benzyl-α-D-glucopyranose (873077-26-0) + acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester (865860-14-6) → allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside (1260731-83-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol1027267

Reference yield: 97.0%

allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside (1260731-83-6) → 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-D-glucopyranose

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol1027267

Reference yield:

allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside (1260731-83-6) → 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate (1260731-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 16 h / 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/ol1027267

upstream raw materials:

allyl 3,4,6-tri-O-benzyl-α-D-glucopyranose

acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester

Downstream raw materials:

3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate

methyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside