3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

Base Information

• Chemical Name: 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
• CAS No.: 378238-76-7
• Molecular Formula: C₂₄H₃₀O₅Si
• Molecular Weight: 426.585
• Mol file: 378238-76-7.mol

Synonyms:3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

Chemical Property of 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

There total 3 articles about 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 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: 96.0%

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane (378238-89-2) → 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (378238-76-7)

Guidance literature:

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane; With acetic acid; In water; at 20 ℃; for 48h;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/ol0167210

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (378238-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / imidazole / dimethylformamide / 18 h

2.1: AcOH / H₂O / 48 h / 20 °C

2.2: 96 percent / NaIO₄ / H₂O; tetrahydrofuran / 5 h / 20 °C

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

DOI:10.1021/ol0167210

Reference yield:

Diacetone D-glucose (2595-05-3) → 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (378238-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / imidazole / dimethylformamide / 18 h

2.1: AcOH / H₂O / 48 h / 20 °C

2.2: 96 percent / NaIO₄ / H₂O; tetrahydrofuran / 5 h / 20 °C

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

DOI:10.1021/ol0167210

upstream raw materials:

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

tert-butylchlorodiphenylsilane

Diacetone D-glucose

Downstream raw materials:

(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-3-benzenesulfinyl-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

N⁶-benzoyladenine

(2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid