1122571-86-1

Basic information

• Product Name: (1'R,3R)-1-(2-benzyl-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H[1,2]oxazin-3-yl)ethane-1,2-diol
• Synonyms: (1'R,3R)-1-(2-benzyl-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H[1,2]oxazin-3-yl)ethane-1,2-diol
• CAS NO: 1122571-86-1
• Molecular Weight: 351.518
• Mol File: 1122571-86-1.mol

Chemical Properties

• CAS DataBase Reference: (1'R,3R)-1-(2-benzyl-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H[1,2]oxazin-3-yl)ethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,3R)-1-(2-benzyl-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H[1,2]oxazin-3-yl)ethane-1,2-diol(1122571-86-1)
• EPA Substance Registry System: (1'R,3R)-1-(2-benzyl-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H[1,2]oxazin-3-yl)ethane-1,2-diol(1122571-86-1)

Safety Data

• Hazardous Substances Data: 1122571-86-1(Hazardous Substances Data)

Upstream product

• 1122571-78-1 C₂₁H₃₃NO₄Si 

Relevant articles and documents

Internally protected amino sugar equivalents from enantiopure 1,2-oxazines: Synthesis of variably configured carbohydrates with C-branched amino sugar units

A stereodivergent synthesis of differently configured C2-branched 4-amino sugar derivatives was accomplished. The Lewis acid mediated rearrangement of phenylthio-substituted 1,2-oxazines delivered glycosyl donor equivalents that can directly be employed in glycosidation reactions. Treatment with methanol provided internally protected amino sugar equivalents that have been transformed into the stereoisomeric methyl glycosides 28, ent-28, 29, ent-29 and 34 in two simple reductive steps. Reaction with natural carbohydrates or bicyclic amino sugar precursors allowed the synthesis of homo-oligomeric di- and trisaccharides 44, 46 and 47 or a hybrid trisaccharide 51 with natural carbohydrates. Access to a bivalent amino sugar derivative 54 was accomplished by reaction of rearrangement product 10 with 1,5-pentanediol. Alternatively, when a protected L-serine derivative was employed as glycosyl acceptor, the glycosylated amino acid 60 was efficiently prepared in few steps. In this report we describe the synthesis of unusual amino sugar building blocks from enantiopure 1,2-oxazines that can be attached to natural carbohydrates or natural product aglycons to produce new natural product analogues with potential applications in medicinal chemistry. Make it simple: A Lewis acid mediated rearrangement of 1,2-oxazines delivers internally protected amino sugar equivalents that can be incorporated into oligosaccharides. Deprotection of the amino sugar precursors by simple reductive steps provides new natural product analogues having C2-branched 4-amino sugar units with different absolute and relative configurations.

Indium trichloride mediated cleavage of acetonides in the presence of acid-labile functional groups - Enhancing the synthetic utility of 1,3-dioxolanyl-substituted 1,2-oxazines

Indium trichloride in an acetonitrile-water mixture chemoselectively cleaved the isopropylidene acetals of various 1,3-dioxolanyl-substituted 1,2-oxazines as well as carbohydrate derivatives. Deprotection of acetonides can be achieved in substrates suscep