allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside

Base Information

• Chemical Name: allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside
• CAS No.: 888958-65-4
• Molecular Formula: C₆₅H₇₄O₁₄
• Molecular Weight: 1079.29

Synonyms:allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside

Chemical Property of allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside

Chemical Property:

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Technology Process of allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside

There total 4 articles about allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside 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: 87.0%

1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose (72657-01-3) + allyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (120022-54-0) → allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside (888958-65-4)

Guidance literature:

1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose; allyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside; With 4 A molecular sieve; dibutyl phosphate; In dichloromethane; at 20 ℃; for 3h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1021/ol0603155

Reference yield:

1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose (72657-01-3) → allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside (888958-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: molecular sieves 4 Angstroem; dibutyl phosphate / CH₂Cl₂ / 3 h / 20 °C

1.2: 88 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.5 h / -40 °C

2.1: 96 percent / NaOMe / methanol / 12 h / 20 °C

3.1: molecular sieves 4 Angstroem; dibutyl phosphate / CH₂Cl₂ / 3 h / 20 °C

3.2: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.5 h / -40 °C

With 4 A molecular sieve; sodium methylate; dibutyl phosphate; In methanol; dichloromethane;

DOI:10.1021/ol0603155

Reference yield:

allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose (119471-45-3) → allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside (888958-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: molecular sieves 4 Angstroem; dibutyl phosphate / CH₂Cl₂ / 3 h / 20 °C

1.2: 88 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.5 h / -40 °C

2.1: 96 percent / NaOMe / methanol / 12 h / 20 °C

3.1: molecular sieves 4 Angstroem; dibutyl phosphate / CH₂Cl₂ / 3 h / 20 °C

3.2: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.5 h / -40 °C

With 4 A molecular sieve; sodium methylate; dibutyl phosphate; In methanol; dichloromethane;

DOI:10.1021/ol0603155

upstream raw materials:

1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose

allyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose

allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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