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

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 294677-69-3
• Molecular Formula: C₇₀H₇₈O₁₅
• Molecular Weight: 1159.38

Synonyms:

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

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

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

There total 7 articles about Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-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:

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,94898-43-8,101966-50-1,143615-35-4,122741-44-0) + Acetic acid (2S,3R,4R,5R,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (294677-68-2) → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (294677-69-3)

Guidance literature:

With 4 A molecular sieve; titanium(IV) fluoride; In diethyl ether; at -78 - 20 ℃; for 15h;

DOI:10.1080/07328300008544096

Reference yield:

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (69850-47-1) → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (294677-69-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / TMSOTf / diethyl ether / -78 - 20 °C

2: 98 percent / MeONa / methanol; CH₂Cl₂ / 15 h / 20 °C / pH 10

3: pTsOH / acetonitrile / 1.5 h / 20 °C

4: aq. AcOH / 1.25 h / 0 °C

5: TiF₄; 4 Angstroem molecular sieves / diethyl ether / 15 h / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; titanium(IV) fluoride; toluene-4-sulfonic acid; acetic acid; In methanol; diethyl ether; dichloromethane; acetonitrile; 1: Condensation / 2: ester cleavage / 3: cyclocondensation / 4: Hydrolysis / 5: Condensation;

DOI:10.1080/07328300008544096

Reference yield:

methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (144174-64-1) → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-4-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (294677-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pTsOH / acetonitrile / 1.5 h / 20 °C

2: aq. AcOH / 1.25 h / 0 °C

3: TiF₄; 4 Angstroem molecular sieves / diethyl ether / 15 h / -78 - 20 °C

With 4 A molecular sieve; titanium(IV) fluoride; toluene-4-sulfonic acid; acetic acid; In diethyl ether; acetonitrile; 1: cyclocondensation / 2: Hydrolysis / 3: Condensation;

DOI:10.1080/07328300008544096

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride

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

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

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

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-(4-O-benzyl-α-L-rhamnopyrnosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

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