phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside

Base Information

• Chemical Name: phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside
• CAS No.: 177263-31-9
• Molecular Formula: C₂₀H₂₈Cl₃NO₃SSi
• Molecular Weight: 496.958

Synonyms:phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside

Chemical Property of phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside

Chemical Property:

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Technology Process of phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside

There total 3 articles about phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside 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: 85.0%

phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (125654-35-5) + trichloroacetonitrile (545-06-2) → phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside (177263-31-9)

Guidance literature:

With sodium hydride; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1055/s-1996-4219

Reference yield:

(2R,3R,6R)-2-Hydroxymethyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran-3-ol (125654-34-4) → phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside (177263-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / imidazole / CH₂Cl₂ / 2 h / Ambient temperature

2: 85 percent / NaH / CH₂Cl₂ / 24 h / Ambient temperature

With 1H-imidazole; sodium hydride; In dichloromethane;

DOI:10.1055/s-1996-4219

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-4-O-(1-imino-1-trichloromethyl)-α-D-threo-hex-2-enopyranoside (177263-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / imidazole / CH₂Cl₂ / 2 h / Ambient temperature

2: 85 percent / NaH / CH₂Cl₂ / 24 h / Ambient temperature

With 1H-imidazole; sodium hydride; In dichloromethane;

DOI:10.1055/s-1996-4219

upstream raw materials:

phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

trichloroacetonitrile

(2R,3R,6R)-2-Hydroxymethyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran-3-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

N-[(2R,3S,4S,5S,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

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

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,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

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