p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 129575-90-2
• Molecular Formula: C₅₁H₅₅NO₁₅
• Molecular Weight: 921.995
• Mol file: 129575-90-2.mol

Synonyms:p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 8 articles about p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 91.0%

Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-4-allyloxy-2-allyloxymethyl-6-chloro-tetrahydro-pyran-3-yl ester (110426-17-0) + p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-89-9) → p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-90-2)

Guidance literature:

With silver trifluoromethanesulfonate; molecular sieve; In 1,2-dichloro-ethane;

DOI:10.1016/0040-4039(90)80026-I

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-90-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / Me₃SiOTf / 1,2-dichloro-ethane / 3 h / 0 °C

2: p-TsOH*H₂O / dimethylformamide / 20 h / 20 °C

3: 61 percent / NaH / dimethylformamide / 20 h / 20 °C

4: 77 percent / p-TsOH*H₂O / methanol; dioxane / 1) 1 h, 60 deg C, 2) 45 min, 85 deg C

6: 91 percent / AgOTf, 4A moleculat sieves / 1,2-dichloro-ethane / -20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84080-P

Reference yield:

4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-43-1) → p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-90-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / NaH / dimethylformamide / 20 h / 20 °C

2: 77 percent / p-TsOH*H₂O / methanol; dioxane / 1) 1 h, 60 deg C, 2) 45 min, 85 deg C

4: 91 percent / AgOTf, 4A moleculat sieves / 1,2-dichloro-ethane / -20 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84080-P

upstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-4-allyloxy-2-allyloxymethyl-6-chloro-tetrahydro-pyran-3-yl ester

p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

p-Methoxyphenyl O-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-Methoxyphenyl O-(6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

O-(2,4-di-O-Benzyl-3-O-levulinoyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

p-Methoxyphenyl O-(2,4-di-O-benzyl-3-O-levulinoyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside