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

Base Information

Chemical Name: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
CAS No.:177263-37-5
Molecular Formula:C₄₂H₅₄Cl₃NO₁₀Si
Molecular Weight:867.336
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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: 65.0%

: 177263-33-1
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

: 177263-37-5
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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In chloroform; for 96h; Ambient temperature;
DOI:10.1055/s-1996-4219

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 177263-37-5
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

Guidance literature:: Multi-step reaction with 6 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

4: 95 percent / NaH / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 80 percent / dimethylformamide / 6 h / 140 °C

6: 65 percent / m-CPBA / CHCl₃ / 96 h / Ambient temperature

With dmap; dichloro bis(acetonitrile) palladium(II); 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1055/s-1996-4219

Reference yield:

: 125654-35-5
phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

: 177263-37-5
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

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / NaH / CH₂Cl₂ / 24 h / Ambient temperature

2: 34 percent / xylene / 24 h / Heating

3: 27 percent / Pd(CH₃CN)2Cl₂, 4A molecular sieves, AgOTf / CH₂Cl₂ / 24 h / Ambient temperature

4: 65 percent / m-CPBA / CHCl₃ / 96 h / Ambient temperature

With dichloro bis(acetonitrile) palladium(II); 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; xylene;
DOI:10.1055/s-1996-4219