Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside
• CAS No.: 138329-03-0
• Molecular Formula: C₃₃H₄₈O₉Si₂
• Molecular Weight: 644.91

Synonyms:Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside

Chemical Property of Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside

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Technology Process of Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside

There total 3 articles about Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-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: 79.0%

Benzoyl bromide (618-32-6) + Methyl 4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-dily)-α-D-glucopyranoside (75156-15-9) → Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside (138329-03-0)

Guidance literature:

With pyridine; at 60 ℃;

DOI:10.1055/s-1992-26291

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside (138329-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 79 percent / pyridine / 60 °C

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1055/s-1992-26291

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → Methyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside (138329-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 79 percent / pyridine / 60 °C

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1055/s-1992-26291

upstream raw materials:

Benzoyl bromide

Methyl 4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-dily)-α-D-glucopyranoside

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 2,3-di-O-benzoyl-4,6-O-<(S)-1-(methoxycarbonyl)ethylidene>-α-D-glucopyranoside

(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzoyloxy-6-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

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