benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside
• CAS No.: 204913-05-3
• Molecular Formula: C₂₅H₂₉NO₇S
• Molecular Weight: 487.574

Synonyms:benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside

Chemical Property:

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Technology Process of benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside

There total 1 articles about benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-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: 100.0%

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide (66026-10-6) + phenylcarbonochloridothioate (1005-56-7) → benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside (204913-05-3)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1081/CAR-120030469

Reference yield: 72.0%

allyltributylstanane (24850-33-7) + benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside (204913-05-3) → benzyl 2-acetamido-3-C-allyl-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranoside (716377-08-1) + Benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-ribo-hexopyranoside

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; at 80 ℃;

DOI:10.1081/CAR-120030469

Reference yield: 16.0%

ethyl acrylate (140-88-5,9003-32-1) + benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-glucopyranoside (204913-05-3) → Benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-ribo-hexopyranoside + Ethyl 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl)propanoate (204913-10-0)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 8h; Heating;

DOI:10.1135/cccc20001726

upstream raw materials:

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

phenylcarbonochloridothioate

Downstream raw materials:

Ethyl 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl)propanoate

benzyl 2-acetamido-3-C-allyl-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranoside

benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-3-C-(penta-2',4'-dienyl)-α-D-glucopyranoside

3-(Benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl)propanoic acid

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