tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane
• CAS No.: 185447-08-9
• Molecular Formula: C₄₄H₅₀O₅SSi
• Molecular Weight: 719.029

Synonyms:tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Chemical Property of tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

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Technology Process of tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

There total 2 articles about tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-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:

methyl 1-thio-α-D-mannopyranoside (80734-76-5) → tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane (185447-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / imidazole / tetrahydrofuran / 8 h / 25 °C

2: 1.) Bu₄NBr, NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, 25 deg C, 8 h

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0968-0896(96)00178-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane (185447-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / imidazole / tetrahydrofuran / 8 h / 25 °C

2: 1.) Bu₄NBr, NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, 25 deg C, 8 h

With 1H-imidazole; tetrabutylammomium bromide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0968-0896(96)00178-2

Reference yield: 22.0%

tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane (185447-08-9) → methyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside (186540-10-3)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 25 ℃; for 8h;

DOI:10.1016/S0968-0896(96)00178-2

upstream raw materials:

methyl 1-thio-α-D-mannopyranoside

tert-butylchlorodiphenylsilane

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-methyl-1-thio-α-D-mannopyranoside

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenoxy)-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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