1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol

Base Information

• Chemical Name: 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol
• CAS No.: 89872-97-9
• Molecular Formula: C₁₉H₃₀O₅Si
• Molecular Weight: 366.53
• Mol file: 89872-97-9.mol

Synonyms:1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol

Chemical Property of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol

There total 6 articles about 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol 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: 58.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol (65190-39-8) → 1,5-anhydro-4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-D-glucitol (89872-96-8) + (4aR,7S,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (89872-97-9)

Guidance literature:

With impramine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jo9718511

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol (89872-97-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / H₂, Triethylamine / Raney nickel / ethyl acetate / 2 h / 50 °C / 51714.8 Torr

2: Triethylamine / methanol; H₂O / 10 h

3: ZnCl₂

4: 1.)Di-n-butyltin oxide, 2.)imidazole / 1.)Toluene, reflux, 4h, 2.)DMF, 70 deg C, 3 h

With 1H-imidazole; hydrogen; di(n-butyl)tin oxide; triethylamine; zinc(II) chloride; nickel; In methanol; water; ethyl acetate;

DOI:10.1021/jo00187a010

Reference yield:

1-deoxy-D-glucose tetraacetate (13137-69-4) → 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol (89872-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Triethylamine / methanol; H₂O / 10 h

2: ZnCl₂

3: 1.)Di-n-butyltin oxide, 2.)imidazole / 1.)Toluene, reflux, 4h, 2.)DMF, 70 deg C, 3 h

With 1H-imidazole; di(n-butyl)tin oxide; triethylamine; zinc(II) chloride; In methanol; water;

DOI:10.1021/jo00187a010

upstream raw materials:

tert-butyldimethylsilyl chloride

1,5-anhydro-4,6-O-(R)-benzylidene-D-glucitol

benzaldehyde

1,5-anhydro-D-glucitol

Downstream raw materials:

N-{9-[(4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-N-isobutyryl-isobutyramide

N-(9-{(3R,4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-pyran-3-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide

2-Amino-9-[(4aR,7R,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-1,9-dihydro-purin-6-one

9-[(4aR,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-6-iodo-9H-purin-2-ylamine