Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 148168-50-7
• Molecular Formula: C₄₄H₅₂O₁₀
• Molecular Weight: 740.891
• Mol file: 148168-50-7.mol

Synonyms:Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

There total 4 articles about Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-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: 80.0%

Acetic acid (2S,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (148168-49-4) → Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (148168-50-7)

Guidance literature:

With methanol; sodium; for 2h;

DOI:10.1016/0008-6215(93)84227-W

Reference yield:

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) → Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (148168-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 3 h / 0 °C

2: 80 percent / Na, MeOH / 2 h

With methanol; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium; In dichloromethane;

DOI:10.1016/0008-6215(93)84227-W

Reference yield:

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-09-4) → Methyl 3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside (148168-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1.5 M H₂SO₄, 2.) pyridine / 1.) 1,4-dioxane, 100 deg C, 18 h

2: 44 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 3 h / 0 °C

3: 80 percent / Na, MeOH / 2 h

With pyridine; methanol; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium; In dichloromethane;

DOI:10.1016/0008-6215(93)84227-W

upstream raw materials:

Acetic acid (2S,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

1,2-Di-O-acetyl-3-O-allyl-4-O-benzyl-α,β-L-rhamnopyranose

Downstream raw materials:

Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

C₅₁H₅₈O₁₀