peracetylated methyl β-cellobioside

Base Information

• Chemical Name: peracetylated methyl β-cellobioside
• CAS No.: 30021-60-4
• Molecular Formula: C₂₇H₃₈O₁₈
• Molecular Weight: 650.588
• Mol file: 30021-60-4.mol

Synonyms:peracetylated methyl β-cellobioside

Chemical Property of peracetylated methyl β-cellobioside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of peracetylated methyl β-cellobioside

There total 3 articles about peracetylated methyl β-cellobioside 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:

methanol (67-56-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((2R,3R,4R,5R,6R)-4-acetoxy-2-acetoxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester (60348-00-7,77068-23-6,77068-25-8,60348-01-8) + acetic acid methyl ester (79-20-9) + methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside (13223-83-1,30021-60-4,30021-61-5,32773-76-5,33054-50-1,52538-76-8,67109-89-1,67310-46-7,81307-80-4,84094-21-3,103188-88-1,114818-00-7,118493-14-4,119433-24-8,119433-25-9,119435-34-6)

Guidance literature:

With tin(IV) chloride; In dichloromethane; for 72h; Molecular sieve; Inert atmosphere;

Reference yield:

methanol (67-56-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8) → acetic acid methyl ester (79-20-9) + hepta-O-acetyl-α-maltosyl chloride (6919-99-9,7166-81-6,14227-58-8,14227-65-7,14543-79-4,58720-13-1,58720-14-2,69283-24-5,127419-32-3) + 1-methyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (13223-83-1,30021-60-4,30021-61-5,32773-76-5,33054-50-1,52538-76-8,67109-89-1,67310-46-7,81307-80-4,84094-21-3,103188-88-1,114818-00-7,118493-14-4,119433-24-8,119433-25-9,119435-34-6)

Guidance literature:

With tin(IV) chloride; In dichloromethane; for 1h; Molecular sieve; Inert atmosphere;

Reference yield:

acetic anhydride (108-24-7) + Phthalic acid 1-((2R,3S,4S,5R,6S)-5-benzoyloxy-3,4-dihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester 2-((2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester → methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-α-D-galactopyranoside (7322-42-1) + methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside (13223-83-1,30021-60-4,30021-61-5,32773-76-5,33054-50-1,52538-76-8,67109-89-1,67310-46-7,81307-80-4,84094-21-3,103188-88-1,114818-00-7,118493-14-4,119433-24-8,119433-25-9,119435-34-6)

Guidance literature:

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; Multistep reaction; 1.) CH₂Cl₂, -78 deg C; 2.) MeOH;

DOI:10.1016/0040-4039(95)02316-X

upstream raw materials:

methanol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate

acetic anhydride

Downstream raw materials:

methyl beta-D-maltoside

methyl β-D-cellobioside

Trifluoro-methanesulfonic acid (2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Methyl 2,3,6,2',3',6'-hexa-O-benzyl-β-D-maltoside

Refernces

• 1、 Valverde, Serafin,Gomez, Ana M.,Lopez, J. Cristobal,Herradon, Bernardo. "Template directed cyclo-glycosylation: Effect of the anchoring sites of the spacer and temperature in the regio-and stereo-selectivity of the glycosylation". . p. 1105 - 1108. Retrieved 2007/10/03.