phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 556039-07-7
• Molecular Formula: C₂₉H₄₀O₆SSi
• Molecular Weight: 544.784

Synonyms:phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

There total 8 articles about phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 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: 70.0%

allyl bromide (106-95-6) + (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol (556039-06-6) → phenyl 2-O-allyl-3-O-tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-07-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1007/s007060200016

Reference yield:

phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-60-3) → phenyl 2-O-allyl-3-O-tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / imidazole / CH₂Cl₂ / 24 h / Heating

2: 70 percent / sodium hydride / dimethylformamide / 2.25 h / 0 - 20 °C

With 1H-imidazole; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120019014

Reference yield:

β-D-glucose (492-61-5) → phenyl 2-O-allyl-3-O-tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (556039-07-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine

1.2: 90 percent / BF₃*Et₂O

2.1: 100 percent / MeONa / methanol

3.1: 94 percent / imidazole

4.1: 70 percent / NaH / dimethylformamide

With 1H-imidazole; sodium methylate; sodium hydride; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1007/s007060200016

upstream raw materials:

allyl bromide

(2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol

tert-butyldimethylsilyl chloride

phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 2-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

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