(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol

Base Information

• Chemical Name: (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol
• CAS No.: 168608-39-7
• Molecular Formula: C21H28O5Si
• Molecular Weight: 388.536
• Mol file: 168608-39-7.mol

Synonyms:(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol

Chemical Property of (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol

Chemical Property:

• Boiling Point: 489.5±45.0 °C(Predicted)
• PSA: 79.15000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 1.00200

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol

There total 4 articles about (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol 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: 78.0%

D-Arabinose (10323-20-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1002/chem.201002895

Reference yield: 75.0%

D-arabinofuranose (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) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7)

Guidance literature:

With pyridine; at 0 - 4 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201300887

Reference yield: 75.0%

D-arabinopyranose (28697-53-2) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7)

Guidance literature:

With pyridine; at 0 - 4 ℃; Inert atmosphere;

DOI:10.1080/07328300903477812

upstream raw materials:

D-arabinofuranose

tert-butyldiphenylsilane

tert-butylchlorodiphenylsilane

D-arabinopyranose

Downstream raw materials:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose

3-deoxy-1,2-O-isopropylidene-β-D-threo-pentofuranose 5-diphenylphosphate

5-O-t-butyldiphenylsilyl-3-O-(imidazolylthiocarbonyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose

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