4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone

Base Information

• Chemical Name: 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone
• CAS No.: 142270-08-4
• Molecular Formula: C₂₆H₃₆O₇SSi
• Molecular Weight: 520.719

Synonyms:4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone

Chemical Property of 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone

Chemical Property:

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Technology Process of 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone

There total 2 articles about 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone 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:

tert-butyldimethylsilyl chloride (18162-48-6) → 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone (142270-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 1) BaO, Ba(OH)2*8H₂O, 2) 85percent 3-chloroperoxybenzoic acid / 1) DMF, 0 deg C, 4 h 2) CH₂Cl₂, 0 deg, 3 h

With 1H-imidazole; barium dihydroxide; 3-chloro-benzenecarboperoxoic acid; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90552-4

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (71676-30-7) → 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone (142270-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 1) BaO, Ba(OH)2*8H₂O, 2) 85percent 3-chloroperoxybenzoic acid / 1) DMF, 0 deg C, 4 h 2) CH₂Cl₂, 0 deg, 3 h

With 1H-imidazole; barium dihydroxide; 3-chloro-benzenecarboperoxoic acid; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90552-4

Reference yield: 80.0%

4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone (142270-08-4) → 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol (142393-19-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

DOI:10.1016/S0008-6215(00)90552-4

upstream raw materials:

tert-butyldimethylsilyl chloride

phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

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