74645-52-6

Basic information

• Product Name: valienamine
• Synonyms: valienamine
• CAS NO: 74645-52-6
• Molecular Weight: 385.371
• Mol File: 74645-52-6.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: valienamine(CAS DataBase Reference)
• NIST Chemistry Reference: valienamine(74645-52-6)
• EPA Substance Registry System: valienamine(74645-52-6)

Safety Data

• Hazardous Substances Data: 74645-52-6(Hazardous Substances Data)

Upstream product

• 202339-50-2 6-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid ethyl ester 
• 202339-63-7 N-[(1S,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3-hydroxymethyl-cyclohex-2-enyl]-4-methyl-benzenesulfonamide 
• 74615-52-4 DL-tri-O-acetyl-(1,3/2,6)-6-bromo-4-bromomethyl-4-cyclohexene-1,2,3-triol 
• 74024-01-4 DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol 
• 108-24-7 acetic anhydride 
• 84270-00-8 N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide 
• 74708-35-3 DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol 
• 227930-76-9 (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 227930-72-5 (1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol 
• 110205-68-0 1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose 
• 1377616-70-0 (3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-hydroxymethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one 
• 1377616-69-7 (3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one 

Downstream Products

• 1447971-22-3 (1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-chloro-4-hydroxycyclohexane-1,2,3-triyl triacetate 
• 1447971-23-4 (1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-iodo-4-hydroxycyclohexane-1,2,3-triyl triacetate 
• 1448147-54-3 (1S,2R,3S,4S,5S,6R)-6-acetamido-4-(acetoxymethyl)-5-bromo-4-hydroxycyclohexane-1,2,3-triyl triacetate 
• 117193-69-8 DL-(1,6/2,3,4,5)-6-acetamido-2-C-acetoxymethyl-1,2,3,4,5-penta-O-acetyl-1,2,3,4,5-cyclohexanepentol 
• 117193-69-8 DL-(1,3,5/2,4,6)-6-acetamido-2-C-acetoxymethyl-1,2,3,4,5-penta-O-acetyl-1,2,3,4,5-cyclohexanepentol 
• 117193-69-8 DL-(1,4/2,3,5,6)-6-acetamido-2-C-acetoxymethyl-1,2,3,4,5-penta-O-acetyl-1,2,3,4,5-cyclohexanepentol 
• 117193-66-5 DL-(1,2,4/3,5,6)-5-acetamido-1-C-acetoxymethyl-2,3,4-tri-O-acetyl-6-bromo-1,2,3,4-cyclohexanetetrol 
• 38231-86-6 valienamine 
• 117193-67-6 DL-(1,2,4,6/3,5)-1-acetamido-3-C-acetoxymethyl-2,4,5-tri-O-acetyl-3-bromo-2,4,5,6-cyclohexanetetrol 
• 84270-00-8 N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide 

Relevant articles and documents

A flexible strategy based on a C2-symmetric pool of chiral substrates: Concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E

A new strategy invoking a new application of the [3,3] sigmatropic rearrangement of allylic azides and the presence of a C2 symmetry element within a pool of chiral substrates was evolved. Not only does this simple flexible strategy provide a concise approach to (+)-valienamine, but it also can readily be adopted for the synthesis of conduramines A-1 and E and the enantiopure azido carbonate 4, a key intermediate of (+)-pancratistatin.

Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: Practical synthesis of (+)-valiolamine

An efficient and practical synthesis of (+)-valiolamine starting from readily available aminocyclitol (+)-valienamine in five steps and up to 80% total yield in gram-scale quantities is reported. Diastereospecific epoxidation by means of substrate directable reaction and regioselective ring-opening of corresponding epoxide are the key reactions in the synthesis, which circumvent laborious purification of products using chromatographical separation. The detailed mechanisms of epoxidation and ring-opening attacked by halide, including the directing and steric hindrance effect, are also discussed.

A concise synthetic approach to (+)-valienamine starting from Garner's aldehyde

A synthesis of (+)-valienamine was achieved starting from Garner's aldehyde in ten steps and 23% overall yield. A unique feature of the synthetic route is that an acyclic precursor was constructed, using diastereoselective antireductive coupling reaction of alkyne and Garner's aldehyde as the key step, which was then cyclized in an intramolecular aldol reaction to form the valienamine skeleton. Georg Thieme Verlag Stuttgart · New York.