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

• 74708-35-3 DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol 
• 38665-10-0 (+)-validoxylamine A 
• 108-24-7 acetic anhydride 
• 74615-52-4 DL-tri-O-acetyl-(1,3/2,6)-6-bromo-4-bromomethyl-4-cyclohexene-1,2,3-triol 
• 77144-65-1 DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol 
• 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 
• 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 
• 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 
• 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

• 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 
• 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 
• 38231-86-6 valienamine 

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 C2-symmetric pool based flexible strategy: An enantioconvergent synthesis of (+)-valiolamine and (+)-valienamine

A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)-valiolamine (1), but it can also be readily adopted for the synthesis of (+)-valienamine (2). Commercially available and cheap C2-symmetric D-tartaric acid served as the chiral building block. Copyright