157733-52-3

Basic information

• Product Name: (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldimethylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide
• Synonyms: (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldimethylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide
• CAS NO: 157733-52-3
• Molecular Weight: 681.983
• Mol File: 157733-52-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldimethylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldimethylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide(157733-52-3)
• EPA Substance Registry System: (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldimethylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide(157733-52-3)

Safety Data

• Hazardous Substances Data: 157733-52-3(Hazardous Substances Data)

Upstream product

• 139627-95-5 (2R,4'S,5'R)-methyl N-<3-(2',2'-dimethyl-5'-vinyl-<1,3>dioxolan-4-yl)-2-hydroxy-propyl>-carbamate 
• 139540-34-4 (2S,4'S,5'R)-methyl N-<3-(2',2'-dimethyl-5'-vinyl-<1,3>dioxolan-4-yl)-2-hydroxy-propyl>-carbamate 
• 157733-35-2 (E)-1-(3'-bromo-4'-methoxy-but-2'-enyloxymethyl)-4-methoxy-benzene 
• 157733-46-5 (2S,2'S,4''S,5''R,3'''Z)-2-<(tert-butyldiphenylsilyl)oxy>-pentanoic acid <3'-<2'',2''-dimethyl-5''-<5'''-(4-methoxy-benzyloxy)-3'''-methoxymethyl-pent-3'''-enyl>-<1'',3''>dioxolan-4''-yl>-2'-methoxymethoxy-propyl>-amide 
• 157733-41-0 (2S,4'S,5'R,3''Z)-methyl N-<3-<2',2'-dimethyl-5'-<5''-(4-methoxy-benzyloxy)-3''-methoxymethyl-pent-3''-enyl>-<1',3'>dioxolan-4'-yl>-2-methoxymethoxy-propyl>-carbamate 
• 157733-45-4 (2S,4'S,5'R,3''Z)-3-<2',2'-dimethyl-5'-<5''-(4'''-methoxy-benzyloxy)-3''-methoxymethyl-pent-3''-enyl>-<1',3'>dioxolan-4'-yl>-2-methoxymethoxy-propylamine 
• 157733-18-1 (2S)-methyl 2-<(tert-butyldiphenylsilyl)oxy>-pentanoate 
• 157733-19-2 (2S)-2-<(tert-butyldiphenylsilyl)oxy>-pentanoic acid 
• 157733-17-0 (2S,5S)-2-tert-butyl-5-propyl-<1,3>dioxolan-4-one 
• 139540-35-5 (2S,4'S,5'R)-methyl N-<3-(2',2'-dimethyl-5'-vinyl-<1',3'>dioxolan-4'-yl)-2-methoxymethoxy-propyl>-carbamate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 157733-51-2 (S)-2-Hydroxy-pentanoic acid ((S)-3-{(4S,5R)-5-[(Z)-5-(4-methoxy-benzyloxy)-3-methoxymethyl-pent-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-propyl)-amide 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 95912-79-1 (2S)-2-Hydroxypentanoic acid methyl ester 

Relevant articles and documents

Total Synthesis of Myxovirescins, 1. Strategy and Construction of the "Southeastern" Part

In this and the following two papers the synthesis of myxovirescins A1, A2 and M2, 28-membered macrocyclic lactam-lactones with antibiotic activity, is described.A retrosynthetic analysis of the myxovirescin family of ca. 30 target molecules leads to a strategy which could be applied to approximately half of them by slight variations of the building blocks used (Schemes 1-3 and following paper).The southeastern part of the molecule, containing the atoms O(1)-C(14) of myxovirescins A and M is described in this first paper (Scheme 3).The assembly is achieved by using the following appropriately protected units: (S)-2-hydroxy-pentanoic acid, (dithian-2-ylmethyl)-amine (Scheme 4), the triflate of (S,R)-2,2-dimethyl-5-vinyl-dioxolan-4-ylmethanol, (E)-3-bromo-2-buten-1-ol, and (E)-2-bromo-2-buten-1,4-diol (Scheme 5), the starting materials for these being malic acid, aminoacetaldehyde, ribose, crotyl alcohol and butyne-1,4-diol.The building blocks are put together by using the following key steps: Kolbe electrolysis, amide formation, lithiodithiane alkylation, and Suzuki coupling (Schemes 6 and 8).The only newly created chirality center is generated stereoselectively by a Li-selectride reduction/Mitsunobu inversion (Table 1, Scheme 7).The termini of the O(1)-C(14) fragment (2 in Scheme 8) carry a (protected) hydroxy acid and an aldehyde group for the Julia coupling and lactonization, respectively, in the final steps of the synthesis.All intermediates are fully characterized.The X-ray crystal structures of two compounds prepared for incorporation as N(4)-C(11) and as C(12)-C(14) of the target molecules are also described (Figures 1 and 2). - Key Words: Myxovirescins / Myxococcus virescens Mx v48 / Suzuki coupling / Macrolides / Lactones / Lactams / 1,3-Dioxolanes / 1,3-Dithianes / Antibiotics