(6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene

Base Information

• Chemical Name: (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene
• CAS No.: 891785-94-7
• Molecular Formula: C₁₈H₂₈O₃Si
• Molecular Weight: 320.504

Synonyms:(6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene

Chemical Property of (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene

Chemical Property:

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Technology Process of (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene

There total 2 articles about (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene 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%

(2R,3S,6S)-2-(hydroxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3-ol (130405-48-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene (891785-94-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol101144k

Reference yield:

(4,6-di-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene (201232-86-2) → (6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene (891785-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NBu₄F*3H₂O / tetrahydrofuran / 2 h / 20 °C

2: 66 percent / imidazole; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.3390/10080859

Reference yield: 76.0%

(6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene (891785-94-7) + 1-bromomethyl-3-methoxybenzene (874-98-6) → tert-butyl(((2R,3S,6S)-3-(3-methoxybenzyloxy)-6-phenyl-3,6-dihydro-2H-pyran-2-yl)methoxy)dimethylsilane (1233959-33-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol101144k

upstream raw materials:

(2R,3S,6S)-2-(hydroxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3-ol

tert-butyldimethylsilyl chloride

(4,6-di-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene

Downstream raw materials:

tert-butyl(((2R,3S,6S)-3-(3-methoxybenzyloxy)-6-phenyl-3,6-dihydro-2H-pyran-2-yl)methoxy)dimethylsilane

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