tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane

Base Information

• Chemical Name: tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane
• CAS No.: 952042-71-6
• Molecular Formula: C₄₅H₅₂O₅SSi
• Molecular Weight: 733.056

Synonyms:tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane

Chemical Property of tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane

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Technology Process of tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane

There total 3 articles about tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane 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: 63.3%

(2R,3S,4S,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triol + benzyl bromide (100-39-0) → tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane (952042-71-6)

Guidance literature:

(2R,3S,4S,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 18h;

DOI:10.2174/1570180817999200618162949

Reference yield:

ethyl 1-thio-α/β-D-glucopyranoside (686299-00-3) → tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane (952042-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 18 h / 20 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.2174/1570180817999200618162949

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyldiphenyl(((2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-6-(ethylthio)tetrahydro-2H-pyran-2-yl)methoxy)silane (952042-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 18 h / 20 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.2174/1570180817999200618162949

upstream raw materials:

ethyl 1-thio-α/β-D-glucopyranoside

tert-butylchlorodiphenylsilane

benzyl bromide

Downstream raw materials:

(2R)-2,3-bis-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 2,3,4-tri-O-benzyl-6-O-(t-butyldiphenylsilyl)-α-D-glucopyranoside

(2R)-2,3-bis-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 2,3,4-tri-O-benzyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

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