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

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 1260731-00-7
• Molecular Formula: C₄₃H₄₂Cl₃NO₆S
• Molecular Weight: 807.235
• Mol file: 1260731-00-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate 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: 97.0%

3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-D-glucopyranose + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate (1260731-00-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol1027267

Reference yield:

allyl 3,4,6-tri-O-benzyl-α-D-glucopyranose (873077-26-0) → 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 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

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

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

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

DOI:10.1021/ol1027267

Reference yield:

acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester (865860-14-6) → 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 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

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

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; 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

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

trichloroacetonitrile

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

Downstream raw materials:

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

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

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