phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 159889-86-8
• Molecular Formula: C₃₇H₄₁NO₁₅S
• Molecular Weight: 771.796
• Mol file: 159889-86-8.mol

Synonyms:phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-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:

phenyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (153889-76-0) → phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159889-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaOMe / methanol; tetrahydrofuran / 2 h / Ambient temperature

2: 1.) camphor sulfonic acid 2.) H₂O / 1.) RT, 2 days, 2.) MeOH, 16 h, reflux

3: pyridine / 16 h / Ambient temperature

With pyridine; camphor-10-sulfonic acid; water; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1016/0008-6215(94)00153-7

Reference yield:

acetic anhydride (108-24-7) + 2-[(2S,3R,4R,5S,6R)-5-((4aR,6S,7R,8R,8aR)-7,8-Dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione → phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159889-86-8)

Guidance literature:

With pyridine; for 16h; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(94)00153-7

Reference yield: 70.0%

benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside (3554-95-8) + phenyl-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159889-86-8) → C48H58N2O22 (159889-87-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -10 ℃; for 0.75h;

DOI:10.1016/0008-6215(94)00153-7

upstream raw materials:

acetic anhydride

phenyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

C₄₈H₅₈N₂O₂₂

C₄₇H₅₆N₂O₂₃

benzyl O-(2,6-di-O-acetyl-3,4-isopropylideno-β-D-galactopyranosyl)-(1<*>4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranoside

benzyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranoside