5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Base Information

• Chemical Name: 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose
• CAS No.: 217309-46-1
• Molecular Formula: C₁₄H₂₈O₅Si
• Molecular Weight: 304.459
• Mol file: 217309-46-1.mol

Synonyms:5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Chemical Property of 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

There total 12 articles about 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 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: 98.0%

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.06.001

Reference yield: 94.0%

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone (75467-36-6) → 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃;

DOI:10.1021/jo00215a036

Reference yield: 90.0%

(1R,4'R,5'S)-(-)-1-(2',2'-dimethyl-5'-vinyl-1',3'-dioxolan-4'-yl)-2-(tert-butyldimethylsilyloxy)-1(R)-ethan-1-ol (116669-77-3) → 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1)

Guidance literature:

With sodium periodate; C₃₁H₂₉Br₂N₃Ru*CH₂Cl₂; water; In ethyl acetate; acetonitrile; at 25 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja5075294

upstream raw materials:

5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone

2,3-O-isopropylidene-D-ribofuranose

tert-butyldimethylsilyl chloride

(2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene

Downstream raw materials:

4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine

benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate

benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl)carbamate

3-benzyl-4-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxazolidin-2-one