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

• 108-24-7 acetic anhydride 
• 38665-10-0 (+)-validoxylamine A 
• 77144-72-0 (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene 
• 70838-35-6 DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 
• 77144-67-3 DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol 
• 86861-73-6 Acetic acid (1R,4S,5S,6S)-4,5-diacetoxy-1-chloro-6-hydroxy-cyclohex-2-enylmethyl ester 
• 81692-14-0 DL-2,3,4-tri-O-acetyl-1,7-anhydro-(1,2,4/3)-1-C-hydroxymethyl-5-cyclohexene-1,2,3,4-tetrol 
• 81692-16-2 DL-tetra-O-acetyl-(1,3/2,4)-4-chloro-4-C-hydroxymethyl-5-cyclohexene-1,2,3-triol 
• 81692-15-1 Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester 
• 74708-35-3 DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-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 
• 84270-00-8 N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide 
• 74615-52-4 DL-tri-O-acetyl-(1,3/2,6)-6-bromo-4-bromomethyl-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 

Downstream Products

• 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 
• 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 
• 117193-66-5 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.

Lewis basic ionic liquid as an efficient and facile catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions

The Lewis basic ionic liquid 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate was employed for the acetylation of various phenols, alcohols, and amines in good-to-excellent yields at 50 C under solvent-free conditions in a short time. Compared with existing methods based on conventional catalysts and toxic solvents, the reported method is simple, mild and environmentally viable. Furthermore, the ionic liquid was conveniently separated from the products and easily recycled to catalyze other acetylation reactions with excellent yields. .

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.