(2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 177263-35-3
• Molecular Formula: C₄₀H₅₄O₉Si
• Molecular Weight: 706.949

Synonyms:(2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

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Technology Process of (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

There total 5 articles about (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 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: 83.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (177263-34-2) → (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (177263-35-3)

Guidance literature:

With dmap; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1055/s-1996-4219

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (177263-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Pd(CH₃CN)2Cl₂, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 89 percent / K₂CO₃ / methanol / 0.75 h / Ambient temperature

3: 83 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); 4 A molecular sieve; silver trifluoromethanesulfonate; potassium carbonate; In methanol; dichloromethane;

DOI:10.1055/s-1996-4219

Reference yield:

phenyl-2,4-di-O-acetyl-2,3-dideoxy-1-thio-α-D-threo-hex-2-eno-pyranoside (125848-19-3,286410-13-7) → (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (177263-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Pd(CH₃CN)2Cl₂, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 89 percent / K₂CO₃ / methanol / 0.75 h / Ambient temperature

3: 83 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); 4 A molecular sieve; silver trifluoromethanesulfonate; potassium carbonate; In methanol; dichloromethane;

DOI:10.1055/s-1996-4219

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

phenyl-2,4-di-O-acetyl-2,3-dideoxy-1-thio-α-D-threo-hex-2-eno-pyranoside

Downstream raw materials:

2,2,2-Trichloro-acetimidic acid (2R,3R,6R)-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester

N-[(2R,3S,6S)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloro-acetamide

N-[(1R,2R,4R,5S,6R)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl]-2,2,2-trichloro-acetamide

N-[(2R,3S,4R,5R,6R)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide

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