p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
• CAS No.: 503303-07-9
• Molecular Formula: C₃₂H₄₀O₇Si
• Molecular Weight: 564.751

Synonyms:p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Chemical Property of p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

Chemical Property:

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Technology Process of p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

There total 4 articles about p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 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: 97.0%

2,2-dimethoxy-propane (77-76-9) + p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside (503303-06-8) → p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (503303-07-9)

Guidance literature:

With [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In acetone; at 20 ℃; for 2h;

DOI:10.1021/jo801171f

Reference yield:

4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (503303-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 2 h

2: 17.2 g / p-TsOH / acetone / 1 h

With pyridine; toluene-4-sulfonic acid; In acetone;

DOI:10.1039/b207509a

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (503303-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: pTsOH / acetone

With pyridine; toluene-4-sulfonic acid; In acetone; 1: Etherification / 2: Etherification;

DOI:10.1016/S0040-4039(99)00911-9

upstream raw materials:

2,2-dimethoxy-propane

p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

4-methoxyphenyl β-D-galactopyranoside

Downstream raw materials:

(3S,4R,5S)-3,4-O-isopropylidene-5-O-p-methoxybenzylhepta-1,6-diene-3,4,5-triol

(2R,3S,4S)-3,4-isopropylidenedioxy-2-benzyloxyhex-5-enal

(Z)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

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