5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

Base Information

• Chemical Name: 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone
• CAS No.: 130222-84-3
• Molecular Formula: C₂₄H₃₀O₅Si
• Molecular Weight: 426.585
• Mol file: 130222-84-3.mol

Synonyms:5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

Chemical Property of 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(3AR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

There total 12 articles about 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 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: 97.0%

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3)

Guidance literature:

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

Reference yield: 82.0%

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3)

Guidance literature:

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201900068

Reference yield: 69.0%

4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol (1449683-05-9) → 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1-deoxy-5,6-O-isopropylidene-D-altro-octo-2,3-diulose (1449682-29-4) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3)

Guidance literature:

With sodium periodate; ruthenium(IV) oxide hydrate; In tetrachloromethane; [⁽²⁾H₆]acetone; water; at 20 ℃; for 0.833333h; Darkness;

DOI:10.1002/chem.201301230

upstream raw materials:

2,3-O-isopropylidene-D-ribonic-γ-lactone

tert-butylchlorodiphenylsilane

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-chloro-pyridin-3-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-chloro-pyridin-3-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

3-<5'-O-<(tert-butyl)diphenylsilyl>-1'-β-hydroxy-2',3'-O-isopropylidene-D-ribofuranosyl>-2,6-dichloropyridine

3-<5'-O-<(tert-butyl)diphenylsilyl>-1'-α-hydroxy-2',3'-O-isopropylidene-D-ribofuranosyl>-2,6-dichloropyridine

Refernces

• 1、 Desaulniers, Jean-Paul,Chang, Yu-Cheng,Aduri, Raviprasad,Abeysirigunawardena, Sanjaya C.,Santalucia Jr., John,Chow, Christine S.. "Pseudouridines in rRNA helix 69 play a role in loop stacking interactions". . p. 3892 - 3895. Retrieved 2008.
• 2、 Dreger, Alexander,Hoff, Katharina,Agoglitta, Oriana,Bülbül, Emre F.,Melesina, Jelena,Sippl, Wolfgang,Holl, Ralph. "Synthesis, biological evaluation, and molecular docking studies of deoxygenated C-glycosides as LpxC inhibitors". . . Retrieved 2021/11/11.