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

Base Information

• Chemical Name: 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
• CAS No.: 148168-49-4
• Molecular Formula: C₄₆H₅₄O₁₁
• Molecular Weight: 782.928
• Mol file: 148168-49-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 44.0%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + 1,2-Di-O-acetyl-3-O-allyl-4-O-benzyl-α,β-L-rhamnopyranose (163660-77-3) → 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)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 3h;

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

Reference yield:

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-09-4) → 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)

Guidance literature:

Multi-step reaction with 2 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

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

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

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

upstream raw materials:

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

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

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

Downstream raw materials:

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

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

C₅₁H₅₈O₁₀