Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 171614-57-6
• Molecular Formula: C₆₄H₇₄O₁₉
• Molecular Weight: 1147.28

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

There total 12 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-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: 90.0%

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) + allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside (171614-54-3) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (171614-57-6)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; dibutyltin chloride; silver trifluoromethanesulfonate; In toluene; at 0 ℃;

DOI:10.1021/jo00125a005

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (171614-57-6)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TsOH / dimethylformamide / 50 °C / reduced pressure

2: 87 percent / 0.1 M TMSOTf / CH₂Cl₂

3: 77 percent / Et₃SiH / trifluoroacetic acid / 0 °C

4: 90 percent / Bu₂SnCl₂, AgOTf, 2,6-di-tert-butyl-4-methylpyridine, 4 A MS / toluene / 0 °C

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; dibutyltin chloride; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; trifluoroacetic acid;

DOI:10.1021/jo00125a005

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5R,6R)-2-allyloxy-3-benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (171614-57-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / TfOH / CH₂Cl₂; cyclohexane

2: K₂CO₃ / methanol

3: p-TsOH / dimethylformamide / 50 °C / reduced pressure

4: 87 percent / 0.1 M TMSOTf / CH₂Cl₂

5: 77 percent / Et₃SiH / trifluoroacetic acid / 0 °C

6: 90 percent / Bu₂SnCl₂, AgOTf, 2,6-di-tert-butyl-4-methylpyridine, 4 A MS / toluene / 0 °C

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; dibutyltin chloride; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; In methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; trifluoroacetic acid;

DOI:10.1021/jo00125a005

upstream raw materials:

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->3(2,6-di-O-benzyl)-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

allyl 2-O-benzyl-(R)-4,6-O-benzylidene-β-D-gluco-pyranoside

Downstream raw materials:

allyl (β-D-galactopyranosyl)1->3[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->4(2,6-di-O-benzyl)]-β-D-glucopyranoside

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