benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 174360-55-5
• Molecular Formula: C₆₃H₇₉NO₃₁
• Molecular Weight: 1346.31
• Mol file: 174360-55-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-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: 52.0%

benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (18404-75-6) + ethyl (2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-4-O-acetyl-2-deoxy-2-phthalimido-1-thio-6-O-trimethylacetyl-β-D-glucopyranoside (174360-54-4) → benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (174360-55-5)

Guidance literature:

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; In dichloromethane; at -10 ℃; for 0.666667h;

DOI:10.1016/0008-6215(95)00319-3

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (174360-55-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / molecular sieves, 2,6-di-O-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂; toluene / 2 h / -10 °C

2: aq. AcOH / 0.5 h / 60 °C

3: pyridine / 16 h / Ambient temperature

4: 0.1 N sodium methoxide, methanol / CH₂Cl₂ / 1.) 40 deg C, 2 min, 2.) RT, 2 h

5: camphorsulfonic acid / 72 h / Ambient temperature

6: pyridine

7: 52 percent / molecular sieves, N-iodosuccinimide, triflic acid / CH₂Cl₂ / 0.67 h / -10 °C

With pyridine; methanol; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; 2,6-di-O-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; toluene;

DOI:10.1016/0008-6215(95)00319-3

Reference yield:

pivaloyl chloride (3282-30-2) → benzyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>3)-(4-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranosyl)-(1<*>3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (174360-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 16 h / Ambient temperature

2: 0.1 N sodium methoxide, methanol / CH₂Cl₂ / 1.) 40 deg C, 2 min, 2.) RT, 2 h

3: camphorsulfonic acid / 72 h / Ambient temperature

4: pyridine

5: 52 percent / molecular sieves, N-iodosuccinimide, triflic acid / CH₂Cl₂ / 0.67 h / -10 °C

With pyridine; methanol; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sodium methylate; In dichloromethane;

DOI:10.1016/0008-6215(95)00319-3

upstream raw materials:

benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

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

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

pivaloyl chloride

Downstream raw materials:

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