101331-92-4

Basic information

• Product Name: 1,3-Dioxolane-4-carboxaldehyde, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,2-dimethyl-, (4R,5S)-
• CAS NO: 101331-92-4
• Molecular Formula: C23H30O4Si
• Molecular Weight: 398.574
• Mol File: 101331-92-4.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxolane-4-carboxaldehyde, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,2-dimethyl-, (4R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolane-4-carboxaldehyde, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,2-dimethyl-, (4R,5S)-(101331-92-4)
• EPA Substance Registry System: 1,3-Dioxolane-4-carboxaldehyde, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,2-dimethyl-, (4R,5S)-(101331-92-4)

Safety Data

• Hazardous Substances Data: 101331-92-4(Hazardous Substances Data)

Usage

Molecular weight

364.55 g/mol

Physical state

Colorless liquid

Stereochemistry

(4R,5S)configuration

Functional groups

a. 1,3-dioxolane ring
b. 4-carboxaldehyde group
c. (1,1-dimethylethyl)diphenylsilyl group
d. Oxy-methyl group

Applications

a. Key intermediate in the synthesis of pharmaceutical and agrochemical products
b. Used in the production of fine chemicals
c. Utilized as a reagent in organic synthesis

Unique molecular structure

The presence of a 1,3-dioxolane ring, a 4-carboxaldehyde group, and a (1,1-dimethylethyl)diphenylsilyl group contribute to its unique properties and make it valuable in various chemical applications.

Upstream product

• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 164105-98-0 (+)-1-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythritol 
• 163964-63-4 Acetic acid (4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 163964-60-1 ((4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) bis-(2,2-dimethylpropanoate) 
• 136136-22-6 ((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 164105-99-1 (4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 136032-73-0 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol 

Downstream Products

• 156145-68-5 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose oxime 
• 366006-22-6 [1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine 
• 871706-58-0 tert-Butyl-((4S,5S)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane 
• 306726-06-7 Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester 
• 147730-61-8 *,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol 

Relevant articles and documents

A facile approach for the total synthesis of neurotrophic diyne tetraol petrosiol A and petrosiol E

The first total synthesis of neurotrophic diacetylenic tetraol, petrosiol A and stereoselective total synthesis of petrosiol E was accomplished. The total synthesis involves Cadiot-Chodkiewicz coupling reaction as the key step for petrosiol A. The diastereorich chiral alcohol (third chiral center) was synthesized from CBS mediated stereoselective ketone reduction reaction for petrosiol E. Of the three chiral centers, the two chiral centers are originated from (+)-diethyl L-tartrate and the third chiral center was generated by an addition reaction of lithium trimethylsilylacetylide leading to two diastereomers which were used for the synthesis of both the natural products and their diastereomer C6-epi-petrosiol A and C6-epi-petrosiol E, respectively.

First total synthesis of neurotrophic diacetylene tetrol (-)-petrosiol D

The first total synthesis of the natural product (-)-petrosiol D has been achieved in a linear fashion. Sharpless asymmetric epoxidation, base induced elimination reaction for the formation of chiral propargyl alcohol and Cadiot-Chodkiewicz coupling react

Toward the stereoselective synthesis of C1-C23 fragment of spirastrellolide B

A convergent synthesis of the protected C(1)-C(23) fragment 4 of the targeted natural product spirastrellolide B is described. The key step of the synthesis is cross metathesis (CM) and TBAF promoted oxa-Michael to construct tetrahydropyran moiety.