Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

Base Information

• Chemical Name: Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane
• CAS No.: 138181-78-9
• Molecular Formula: C₃₀H₃₇ClO₆Si
• Molecular Weight: 557.159
• Mol file: 138181-78-9.mol

Synonyms:Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

Chemical Property of Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

There total 2 articles about Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-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 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + dimethylsilicon dichloride (75-78-5,30107-43-8) → Chloro-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-78-9)

Guidance literature:

With n-butyllithium; Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C to RT;

DOI:10.1021/ja00029a047

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) + dimethylsilicon dichloride (75-78-5,30107-43-8) → Chloro-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-78-9)

Guidance literature:

With n-butyllithium; Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C to RT;

DOI:10.1021/ja00029a047

Reference yield: 100.0%

(3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (354114-14-0) + Chloro-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-78-9) → ((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (138181-79-0,138256-55-0)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 0.166667h; Ambient temperature;

DOI:10.1021/ja00029a047

upstream raw materials:

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

dimethylsilicon dichloride

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

((3S,4S,5R,6R)-2-Benzenesulfinyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane

((3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane