methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 441777-59-9
• Molecular Formula: C₄₅H₅₉NO₁₄
• Molecular Weight: 837.962
• Mol file: 441777-59-9.mol

Synonyms:

Chemical Property of methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 7 articles about methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 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:

methyl (4-O-benzyl-2,3-di-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-57-7) → methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-59-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 7h; pH=10;

DOI:10.1016/S0040-4020(02)00148-5

Reference yield:

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside (69558-07-2) → methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-59-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / AgOTf; 2,6-di-tert-butyl-4-methyl pyridine / CH₂Cl₂ / -50 - 20 °C

2.1: ethylendiamine / ethanol / 9 h / 70 °C

2.2: 83 percent / ethanol / 2 h / 20 °C

3.1: 6.88 g / PTSA / acetone / 20 °C

4.1: 971 mg / TMSOTf / diethyl ether / -78 - 20 °C

5.1: 1.53 g / 1N sodium methoxide / methanol / 7 h / 20 °C / pH 10

With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; ethylenediamine; In methanol; diethyl ether; ethanol; dichloromethane; acetone;

DOI:10.1016/S0040-4020(02)00148-5

Reference yield:

methyl (2-amino-2-deoxy-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-52-2) → methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 59 percent / methanol / 1.25 h / 20 °C

2: 6.88 g / PTSA / acetone / 20 °C

3: 971 mg / TMSOTf / diethyl ether / -78 - 20 °C

4: 1.53 g / 1N sodium methoxide / methanol / 7 h / 20 °C / pH 10

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; diethyl ether; acetone;

DOI:10.1016/S0040-4020(02)00148-5

upstream raw materials:

methyl (4-O-benzyl-2,3-di-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl (2-amino-2-deoxy-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthaloylamino-β-D-glucopyranosyl bromide

Downstream raw materials:

acetic acid 2-[7-acetylamino-6-(4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester