137649-69-5

Basic information

• Product Name: (2S,3R,4R,5S)-2,5-bis<<(benzyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane
• Synonyms: (2S,3R,4R,5S)-2,5-bis<<(benzyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane
• CAS NO: 137649-69-5
• Molecular Weight: 568.67
• Mol File: 137649-69-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R,5S)-2,5-bis<<(benzyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R,5S)-2,5-bis<<(benzyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane(137649-69-5)
• EPA Substance Registry System: (2S,3R,4R,5S)-2,5-bis<<(benzyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane(137649-69-5)

Safety Data

• Hazardous Substances Data: 137649-69-5(Hazardous Substances Data)

Upstream product

• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 75-36-5 acetyl chloride 
• 3182-95-4 L-Phenylalaninol 
• 501-53-1 benzyl chloroformate 
• 136740-99-3 1-[5-(1-amino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 147879-43-4 N'-((S)-1-{(4R,5R)-5-[(S)-1-(N',N'-Dimethyl-hydrazino)-2-phenyl-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-phenyl-ethyl)-N,N-dimethyl-hydrazine 

Downstream Products

• 140196-57-2 {1-[5-(1-benzyloxycarbonylamino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 143747-07-3 (2S,3R,4R,5S)-3-acetoxy-2,5-bis<<(benzyloxy)carbonyl>amino>-4-hydroxy-1,6-diphenylhexane 
• 143747-08-4 (2S,3R,4R,5S)-3-acetoxy-2,5-bis<<(benzyloxy)carbonyl>amino>-4-<(methanesulfonyl)oxy>-1,6-diphenylhexane 
• 143747-09-5 (4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-<1-<<(benzyloxy)carbonyl>amino>-2-phenylethyl>-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one 
• 143838-09-9 (4S,5R,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one) 
• 134878-07-2 (2S,3R,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane 
• 170117-42-7 (4R,5R,1''S)-1-methyl-1-(3'-carboxypropyl)-4,5-bis<1''-amino-2''-phenylethyl>-1,3-dioxolane 
• 1004316-58-8 C₃₅H₃₄N₂O₆S 
• 137649-75-3 (4S,5R,4'S,5'R)-5,5'-bis(4-benzyloxazolidin-2-one) 
• 100-51-6 benzyl alcohol 
• 137649-86-6 (2S,3R,4R,5S)-2,5-Diamino-1,6-diphenyl-3,4-hexanediol Dihydrochloride 
• 134805-49-5 (2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane 
• 137649-81-1 (4S,5R,4'S,5'R)-4,4'-Dibenzyl-3,3'-bis-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-[5,5']bioxazolidinyl-2,2'-dione 
• 143747-06-2 (4S,5S,1'R,2'S)-5-<1-acetoxy-2-<<(benzyloxy)carbonyl>amino>-3-phenylpropyl>-4-benzyloxazolidin-2-one 

Relevant articles and documents

Expedient solid-phase synthesis of both symmetric and asymmetric diol libraries targeting aspartic proteases

C2-symmetric diols have been shown to be highly potent against HIV-1 protease (PR). However, gaining access to these compounds has been hampered by the need of multistep solution-phase reactions which are often tedious and inefficient. In this Letter, we have disclosed a solid-phase strategy for rapid preparation of small molecule-based, symmetric and asymmetric diols as potential HIV-1 protease inhibitors. Upon biological screening, we found one of them, SYM-5, to be a potent and selective inhibitor (Ki = 400 nM) against HIV-1 protease.

Method for synthesis of C2-symmetric diamino diol mediated by titanium complexes

A method for synthesis of C2-symmetric diamino diol mediated by titanium complexes is provided. A substituted-L-phenylalaninal undergoes pinacol coupling to yield the corresponding C2-symmetric (1S,2R,3R,4S)-1,4-diamino 2,3-diol in the presence of Cp2TiCl2/ZnCl2 and zinc metal, mediated in good yield and highly selective. This titanium-catalyzed reaction yields diaminodiol, offering a convenient alternative method to the synthesis of C2-symmetric peptidic protease inhibitors. Consequently, the method allows to synthesize TL-3 via titanium complex in moderate yield.

Pharmaceutical composition

A solid pharmaceutical composition is disclosed which comprises a pharmaceutically acceptable adsorbent or a mixture of pharmaceutically acceptable adsorbents to which is adsorbed a mixture of (1) a pharmaceutically acceptable organic solvent or a mixture of pharmaceutically acceptable organic solvents, (2) an HIV protease inhibiting compound and (3) one or more pharmaceutically acceptable acids. The solid composition can optionally be encapsulated in a hard gelatin capsule.