1006032-29-6

Basic information

• Product Name: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol
• Synonyms: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol
• CAS NO: 1006032-29-6
• Molecular Weight: 586.8
• Mol File: 1006032-29-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol(1006032-29-6)
• EPA Substance Registry System: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol(1006032-29-6)

Safety Data

• Hazardous Substances Data: 1006032-29-6(Hazardous Substances Data)

Upstream product

• 89747-54-6 (3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 1320269-76-8 (3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 152006-17-2 2,3-O-isopropylidene-L-lyxono-1,4-lactone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 124-63-0 methanesulfonyl chloride 
• 1006364-60-8 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-L-lyxitol 

Downstream Products

• 1006032-30-9 (3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole 
• 1320269-77-9 tert-butyl (((3aS_.4R_.6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane 
• 596103-06-9 ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol 
• 1006032-31-0 C₂₄H₃₂O₄SeSi 
• 1006032-32-1 acetic acid 6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl ester 
• 1433368-87-6 7-[6-(tert-butyl-diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-6-chloro-7H-purin-2-ylamine 
• 1433368-95-6 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine 
• 1433368-79-6 7-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-5-selena-pentalen-4-yl]-6-chloro-7H-purine 
• 1433368-71-8 9-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-1,3-dioxa-5-selena-pentalen-4-yl]-6-chloro-9H-purine 
• 1433369-48-2 2-amino-9-[6-((tert-butyl)diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-1,9-dihydropurin-6-one 
• 1146697-60-0 1-hydroxy-2-trityloxymethyl-1,2,3a,8a-tetrahydro-8-oxa-3-selena-3b,7-diazacyclopenta[a]inden-6-one 
• 1620879-61-9 (-)-2,2'-anhydro-1-(5-O-trityl-4-seleno-D-arabinofuranosyl)thymine 
• 1620879-62-0 (-)-2,2'-anhydro-5-fluoro-1-(5-O-trityl-4-seleno-D-arabinofuranosyl)uracil 
• 1620879-63-1 (-)-2,2'-anhydro-5-chloro-1-(5-O-trityl-4-seleno-D-arabinofuranosyl)uracil 

Relevant articles and documents

Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar

The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.

New RNA purine building blocks, 4'-selenopurine nucleosides: First synthesis and unusual mixture of sugar puckerings

Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.

First synthesis of 4′-selenonucleosides showing unusual southern conformation

(Chemical Equation Presented) The first synthesis of 4′- selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4′-oxonucleosides were overwhelmed by the size of selenium and steric interacti