phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 679800-18-1
• Molecular Formula: C₃₃H₄₀O₁₄S
• Molecular Weight: 692.738
• Mol file: 679800-18-1.mol

Synonyms:phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside

There total 12 articles about phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-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:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-pyran-3-yl ester → phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside (679800-18-1)

Guidance literature:

With acetic acid; In water; at 70 ℃; for 4h;

DOI:10.1081/SCC-120027259

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside (679800-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / hydrazine; AcOH / dimethylformamide / 2 h / 50 °C

2: 59 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

3: Et₂O*BF₃ / CH₂Cl₂ / 2 h / 0 °C

4: AcOH / H₂O / 4 h / 70 °C

With boron trifluoride diethyl etherate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1081/SCC-120027259

Reference yield:

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) → phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-benzyl-1-thio-β-D-glucopyranoside (679800-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

2: Et₂O*BF₃ / CH₂Cl₂ / 2 h / 0 °C

3: AcOH / H₂O / 4 h / 70 °C

With boron trifluoride diethyl etherate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water;

DOI:10.1081/SCC-120027259

upstream raw materials:

D-glucose pentaacetate

2,3,4,5-tetra-O-acetyl-D-glucopyranose

benzyl-O-β-D-glucopyranoside

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->6)]-3-O-benzyl-1-thio-β-D-glucopyranoside