Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester
• CAS No.: 881425-86-1
• Molecular Formula: C₃₇H₅₅NO₁₅Si
• Molecular Weight: 781.927

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 48.0%

N-{(2R,4aR,6S,7R,8R,8aS)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide + O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate (74808-10-9,86520-63-0,92052-29-4,121238-27-5,127061-80-7,142831-80-9,87119-53-7) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester (881425-86-1)

Guidance literature:

DOI:10.1039/b210503a

Reference yield:

Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-(2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxycarbonylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester (881425-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: sodium methoxide / methanol / 2 h / 20 °C

3: 72 percent / camphorsulfonic acid / acetonitrile / 3 h / 20 °C

4: 85 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves AW / CH₂Cl₂ / 0.75 h / -20 °C

5: 82 percent / triethylamine / sonification

With 1H-imidazole; molecular sieve; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Zemplen deacetylation;

DOI:10.1021/ol060006e

Reference yield:

{(2R,4aR,6S,7R,8R,8aS)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid 2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester (881425-84-9) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(2R,4aR,6S,7R,8R,8aS)-7-acetylamino-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester (881425-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves AW / CH₂Cl₂ / 0.75 h / -20 °C

2: 82 percent / triethylamine / sonification

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1021/ol060006e

upstream raw materials:

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

{(3R,4R,5S,6R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester

{(2R,4aR,6S,7R,8R,8aS)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid 2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl ester

Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-(2-bromo-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxycarbonylamino)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-tetrahydro-pyran-4-yl ester

Downstream raw materials:

C₆₂H₉₀N₂O₃₄

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