methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside
• CAS No.: 160083-39-6
• Molecular Formula: C₄₈H₄₆O₁₉S₂
• Molecular Weight: 991.014
• Mol file: 160083-39-6.mol

Synonyms:methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside

There total 6 articles about methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-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:

p-benzoquinone (106-51-4) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside (160083-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) PhI(OAc)2 / 1.) MeOH, 1 h, r.t., 2.) MeOH, 30 min, r.t.

2: 2.) PhI(OAc)2 / 1.) acetone, MeOH, 30 min, r.t., 2.) acetone, MeOH, 30 min, r.t.

With [bis(acetoxy)iodo]benzene;

DOI:10.1002/hlca.19940770319

Reference yield:

methyl 2,3,6-tri-O-benzoyl-4-thio-α-D-glucopyranoside (118868-80-7,79580-71-5) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside (160083-39-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) Na₂S₂O₄ / 1.) MeOH, 30 min, r.t., 2.) CHCl₃, H₂O, 5 min, r.t.

2: 93 percent / Ag₂O, Na₂SO₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 2.) PhI(OAc)2 / 1.) acetone, MeOH, 30 min, r.t., 2.) MeOH, 30 min, r.t.

With sodium dithionite; [bis(acetoxy)iodo]benzene; sodium sulfate; silver(l) oxide; In dichloromethane;

DOI:10.1002/hlca.19940770319

Reference yield:

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(2',5'-dihydroxyphenylthio)-α-D-glucopyranoside (160083-37-4) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxo-4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)cyclohexa-1',4'-dienylthio)-α-D-glucopyranoside (160083-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Ag₂O, Na₂SO₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 2.) PhI(OAc)2 / 1.) acetone, MeOH, 30 min, r.t., 2.) MeOH, 30 min, r.t.

With [bis(acetoxy)iodo]benzene; sodium sulfate; silver(l) oxide; In dichloromethane;

DOI:10.1002/hlca.19940770319

upstream raw materials:

tetraacetyl thioglucose

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-(3',6'-dioxocyclohexa-1',4'-dienylthio)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-4-thio-α-D-glucopyranoside

2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)benzo-1,4-quinone

Downstream raw materials:

methyl 4-deoxy-4-<4'-(β-D-glucopyranosylthio)-2',5'-dihydroxyphenylthio>-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-<4'-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosylthio)-2',5'-dihydroxyphenylthio>-α-D-glucopyranoside