1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose
• CAS No.: 114861-14-2
• Molecular Formula: C24H32O5Si
• Molecular Weight: 428.601
• Mol file: 114861-14-2.mol

Synonyms:5-O-(T-BUTYLDIPHENYLSILYL)-1,2-O-ISOPROPYLIDENE-A-D-XYLOFURANOSE;

Chemical Property of 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose

Chemical Property:

• Boiling Point: 495.5±45.0 °C(Predicted)
• PKA: 13.17±0.60(Predicted)
• PSA: 57.15000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 2.80030

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose

There total 9 articles about 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose 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: 100.0%

1,2-O-isopropylidene-α-D-xylose (20031-21-4) + tert-butylchlorodiphenylsilane (58479-61-1) → 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose (114861-14-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1.16667h; Inert atmosphere;

DOI:10.1002/anie.201310569

Reference yield: 99.3%

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) + tert-butylchlorodiphenylsilane (58479-61-1) → 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose (114861-14-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(98)00135-9

Reference yield:

D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose (114861-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / conc. H₂SO₄ / 1.) 25 deg C, 6h, 2.) MeOH, 25 deg C, 2h

2: 96 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

With 1H-imidazole; sulfuric acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja00241a062

upstream raw materials:

1,2-O-isopropylidene-α-D-xylose

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

D-xylose

Downstream raw materials:

tert-Butyl-((3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane

1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose

[(3aR,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-acetic acid ethyl ester