104874-61-5

Usage

InChI:InChI=1/C8H16O5/c1-4-5(9)8(2,11)6(10)7(12-3)13-4/h4-7,9-11H,1-3H3/t4-,5-,6-,7+,8+/m0/s1

Upstream product

• 115957-14-7 methyl 4-O-benzoyl-6-deoxy-3-C-methyl-α-L-mannopyranoside 
• 74995-86-1 methyl 4-O-benzoyl-2,3,6-trideoxy-3C-methyl-D-erythro-hex-2-enopyranoside 
• 90329-14-9 methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-α-L-lyxo-hexopyranosid-4-ulose 
• 104846-14-2 4,5-dihydroxy-6-methoxy-2,4-dimethyldihydropyran-3-one 
• 79366-18-0 methyl 2,3-di-O-benzyl-6-deoxy-3-C-methyl-α-D-allopyranoside 

Downstream Products

• 93474-76-1 methyl 4,6-dideoxy-3-C-methyl-4-(N-methyl-N-phenylsulfonylamino)-α-L-mannopyranoside 

Relevant academic research and scientific papers

Unusual sugars of the GPL-type antigen of Mycobacterium avium serovar 19. Stereoselective synthesis of methyl 6-deoxy-3-C-methyl-2,4-di-O-methyl-α-L-mannopyranoside and its C-4 epimer

Completely reversed stereoselectivity of reduction of methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-α-L-mannopyranoside (2) and its deisopropylidenated derivative (7) was observed. Compound 2 gave exclusively the L-talo-isomer (3) with NaBH4 in MeOH, but the reduction of 7 with NaBH4 in acetic acid resulted in the L-manno-derivative 8. It is assumed that in the first case the stereoselectivity is determined by the steric accessibility of the carbonyl group, while in the second case free OH-groups direct the selectivity of the reduction by complexation or ligand exchange.

Phorbasides A-E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations

(Chemical Equation Presented) Five new cytotoxic macrolide glycosides phorbasides A-E (3-7), each possessing a macrolide ring appended to a rare ene-yne-trans-2-chlorocyclopropane, were isolated from the same Western Australian sponge (Phorbas sp.) that provided phorboxazoles A and B. The structures of 3-7 were solved by analysis of spectroscopic data including NMR, MS, and CD. A synthesis of methyl 2-O-methyl-α-L-evalose from L-rhamnose was completed and used for configurational assignment of the sugar residue in 3. Acid-catalyzed methanolysis of 3 followed by two-step derivatization of the liberated O-methyl glycoside gave a vicinal 4-O-naphthoyl/tertiary 3-N-(2-aminonaphthyl)carbamate derivative that exhibited exciton coupled CD identical with that of the derivative prepared from synthetic 1,2-O-dimethyl-α-L-evalose.