(3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole

Base Information

• Chemical Name: (3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole
• CAS No.: 153172-31-7
• Molecular Formula: C14H29 N O3 Si
• Molecular Weight: 287.475
• DSSTox Substance ID: DTXSID201107065
• Nikkaji Number: J2.914.530J
• Mol file: 153172-31-7.mol

Synonyms:153172-31-7;(3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole;(3aR,4R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole;[(3aR,4R,6aS)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methoxy-tert-butyl-dimethylsilane;SCHEMBL4067627;DTXSID201107065;PS-16973;CS-0016281;P10778;(3AR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole;(3AR,4R,6AS)-4-(TERT-BUTYL-DIMETHYL-SILANYLOXYMETHYL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE;(3aR,4R,6aS)-4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-4H-1,3-dioxolo[4,5-c]pyrrole

Chemical Property of (3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole

Chemical Property:

• PSA: 39.72000
• LogP: 2.82890
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 287.19167032
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

97% ^*data from raw suppliers

5-O-tert-Butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2CNC(C2O1)CO[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: CC1(O[C@H]2CN[C@@H]([C@H]2O1)CO[Si](C)(C)C(C)(C)C)C

Technology Process of (3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole

There total 15 articles about (3aR,4R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole 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: 80.0%

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol (153172-30-6) → (3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; for 6h;

DOI:10.1016/j.bmc.2011.07.043

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

2: H₂ / 10 percent Pd-C / ethanol / 1551.4 Torr

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)79290-2

Reference yield:

N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (117858-84-1) → (3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

2: H₂ / 10 percent Pd-C / ethanol / 1551.4 Torr

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)79290-2

upstream raw materials:

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol

tert-butyldimethylsilyl chloride

N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

C₈H₁₅NO₃

Downstream raw materials:

tert-butyl (3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

tert-butyl (3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-6-{3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}-2,2-dimethyl-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

(2E)-N-[4-(1-benzoylpiperidin-4-yl)butyl]-3-{3-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]phenyl}prop-2-enamide hydrochloride

(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR INHIBITING VIRAL POLYMERASE". Page/Page column 78. . Retrieved 2013/11/05.
• 2、 Malladi, Venkata L.A.,Sobczak, Adam J.,Meyer, Tiffany M.,Pei, Dehua,Wnuk, Stanislaw F.. "Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring". experimental part. p. 5507 - 5519. Retrieved 2011/11/06.