phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside
• CAS No.: 1353015-60-7
• Molecular Formula: C₃₄H₄₄O₇SSi
• Molecular Weight: 624.871

Synonyms:phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

There total 1 articles about phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-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: 89.0%

phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside (795305-86-1) + tert-butylchlorodiphenylsilane (58479-61-1) → phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (1353015-60-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201100934

Reference yield: 58.0%

phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (1353015-60-7) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → phenyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1->2)-6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (1353015-61-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201100934

Reference yield:

phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (1353015-60-7) → phenyl 6-O-tert-butyldiphenylsilyl-3,4-O-(2′,3′-dimethoxybutane-2′3′-diyl)-1-thio-β-D-arabino-hexopyranoside-2-ulose

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.201600526

upstream raw materials:

phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside

tert-butylchlorodiphenylsilane

Downstream raw materials:

methyl (2R)-3-(tert-butyldiphenylsilyloxy)-2-[2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1->2)-6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-glucopyranosyloxy]propanoate

phenyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1->2)-6-O-(tert-butyldiphenylsilyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

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