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

Base Information

• Chemical Name: 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
• CAS No.: 1260731-05-2
• Molecular Formula: C₆₉H₇₂O₁₁S
• Molecular Weight: 1109.39
• Mol file: 1260731-05-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate (1260731-00-7) → 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 (1260731-05-2) + 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 (1260731-67-6)

Guidance literature:

3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate; In dichloromethane; at 20 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 0.666667h; Inert atmosphere;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -78 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol1027267

Reference yield:

allyl 3,4,6-tri-O-benzyl-α-D-glucopyranose (873077-26-0) → 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 (1260731-05-2) + 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 (1260731-67-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 0.67 h / -78 - 0 °C / Inert atmosphere

4.3: 16 h / -78 - 20 °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:

allyl 3,4,6-tri-O-benzyl-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranoside (1260731-83-6) → 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 (1260731-05-2) + 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 (1260731-67-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 0.67 h / -78 - 0 °C / Inert atmosphere

3.3: 16 h / -78 - 20 °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:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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

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