Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside

Base Information

• Chemical Name: Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside
• CAS No.: 78329-10-9
• Molecular Formula: C₂₀H₃₀O₆Si
• Molecular Weight: 394.54

Synonyms:Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside

Chemical Property of Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside

Chemical Property:

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Technology Process of Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside

There total 3 articles about Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside 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:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside (78329-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / pyridine / 72 h / Ambient temperature

2: 77 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane;

DOI:10.1016/0008-6215(92)84176-S

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside (78329-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / pyridine / 72 h / Ambient temperature

2: 77 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane;

DOI:10.1016/0008-6215(92)84176-S

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside (78329-10-9) + Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside (78342-32-2)

Guidance literature:

With oxygen; Multistep reaction;

DOI:10.1021/jo00331a050

upstream raw materials:

tert-butyldimethylsilyl chloride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Downstream raw materials:

Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-2-deoxy-2-C-(methoxycarbonylmethylene)-α-D-ribo-hexopyranoside

Methyl 4,6-O-Benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-α-D-allopyranoside

Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(((vinyloxy)methyl)methylene)-α-D-ribo-hexopyranoside

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