2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS No.: 904690-70-6
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583

Synonyms:2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 2 articles about 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 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: 99.0%

benzyl bromide (100-39-0) + 2-(trimethylsilyl)ethyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (151072-02-5) → 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (904690-70-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1016/j.carres.2006.04.006

Reference yield:

2-(Trimethylsilyl)ethyl α-L-rhamnopyranoside (146934-36-3) → 2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (904690-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / camphorsulfonic acid / 4 h / 22 °C

2: 99 percent / NaH / dimethylformamide / 1 h

With camphor-10-sulfonic acid; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.04.006

Reference yield:

2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (904690-70-6) → (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4-diol

Guidance literature:

With acetic acid; In water; at 65 ℃; for 2h;

DOI:10.1016/j.carres.2006.04.006

upstream raw materials:

benzyl bromide

2-(trimethylsilyl)ethyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

2-(Trimethylsilyl)ethyl α-L-rhamnopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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