302917-23-3

Basic information

• Product Name: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tetrahydro-furan-3-yl ester
• Synonyms: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tetrahydro-furan-3-yl ester
• CAS NO: 302917-23-3
• Molecular Weight: 658.7
• Mol File: 302917-23-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tetrahydro-furan-3-yl ester(302917-23-3)
• EPA Substance Registry System: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-tetrahydro-furan-3-yl ester(302917-23-3)

Safety Data

• Hazardous Substances Data: 302917-23-3(Hazardous Substances Data)

Upstream product

• 40554-98-1 [(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate 
• 302917-21-1 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 100-39-0 benzyl bromide 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 302917-27-7 Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(R)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 302917-25-5 {(3aR,4R,6S,6aR)-6-[(R)-2-Benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-methanol 

Relevant articles and documents

Synthesis of the nucleoside moiety of liposidomycins: Elucidation of the pharmacophore of this family of MraY inhibitors

Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50 = 50 μM). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50 = 5 μM). (C) 2000 Elsevier Science Ltd. All rights reserved.