N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol

Base Information

• Chemical Name: N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol
• CAS No.: 171077-35-3
• Molecular Formula: C₃₅H₄₇NO₇Si
• Molecular Weight: 621.846

Synonyms:N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol

Chemical Property of N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol

Chemical Property:

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MSDS Files:

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Technology Process of N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol

There total 1 articles about N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol 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%

tert-butyldimethylsilyl chloride (18162-48-6) + N-benzyloxycarbonyl-1,5-di-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol → N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol (171077-35-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at -40 ℃; for 2h;

DOI:10.1248/cpb.43.414

Reference yield: 10.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) + N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol (171077-35-3) → (2R,3R,4R,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1248/cpb.43.414

Reference yield: 7.0%

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (74808-09-6,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,114743-70-3,132201-75-3,132748-02-8,83441-60-5) + N-benzyloxycarbonyl-1,5-di-O-benzyl-7-O-tert-butyldimethylsilyl-2,6-dideoxy-2,6-imino-D-glycero-D-talo-heptitol (171077-35-3) → (2R,3R,4R,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1248/cpb.43.414

upstream raw materials:

tert-butyldimethylsilyl chloride

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