6217-21-6

Basic information

• Product Name: 1-O-Methyl-2-O,3-O,4-O-triacetyl-5,6-didehydro-6-deoxy-α-D-glucopyranose
• Synonyms: 1-O-Methyl-2-O,3-O,4-O-triacetyl-5,6-didehydro-6-deoxy-α-D-glucopyranose;Methyl 2-O,3-O,4-O-triacetyl-6-deoxy-α-D-xylo-5-hexenopyranoside;Methyl 2-O,3-O,4-O-triacetyl-6-deoxy-α-D-xylo-hexa-5-enopyranoside
• CAS NO: 6217-21-6
• Molecular Formula: C₁₃H₁₈O₈
• Molecular Weight: 302.27722
• Mol File: 6217-21-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O-Methyl-2-O,3-O,4-O-triacetyl-5,6-didehydro-6-deoxy-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Methyl-2-O,3-O,4-O-triacetyl-5,6-didehydro-6-deoxy-α-D-glucopyranose(6217-21-6)
• EPA Substance Registry System: 1-O-Methyl-2-O,3-O,4-O-triacetyl-5,6-didehydro-6-deoxy-α-D-glucopyranose(6217-21-6)

Safety Data

• Hazardous Substances Data: 6217-21-6(Hazardous Substances Data)

Upstream product

• 59578-04-0 methyl 2,3,4-tri-O-trimethylsilyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 5155-46-4 methyl 6-iodo-6-deoxy-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 20771-10-2 1-O-methyl-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 6984-65-2 methyl 2,3,4-tri-O-trimethylsilyl-5-methylene-α-D-xylopyranoside 
• 110-86-1 pyridine 
• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 

Downstream Products

• 87940-06-5 (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-hydroxy-cyclohexanone oxime 
• 87984-31-4 (2S,3R,4S,5R) 5-hydroxy-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 87940-07-6 (1S,2R,3R,4S,5R)-2,3,4-Tri-O-benzylcyclohexane-1,2,3,4,5-pentol 
• 87940-07-6 (1R,2R,3R,4S,5S)-2,3,4-Tri-O-benzylcyclohexane-1,2,3,4,5-pentol 
• 87940-07-6 (1R,2R,3R,4S,5R)-2,3,4-Tri-O-benzylcyclohexane-1,2,3,4,5-pentol 
• 87984-35-8 (2-L-1,3/2,4,5)-1-amino-2,3,4-tri-O-benzyl-2,3,4,5-cyclohexanetetrol 
• 87940-08-7 (2-L-1,2,4,5/3)-1-amino-2,3,4-tri-O-benzyl-2,3,4,5-cyclohexanetetrol 
• 85716-45-6 1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon 
• 439614-80-9 1-O-(2-bromobenzoyl)-2,3,4-tri-O-benzyl-β-D-xylohexoseptanosid-5-ulose 
• 439614-74-1 (3S,5S,6R,7R,8S)-6,7,8-Tris-benzyloxy-5-methoxy-1,4-dioxa-spiro[2.5]octane 
• 316172-40-4 2,3,4-tri-O-benzyl-5-O-tert-butyldimethylsilyl-1,6-anhydro-β-L-idopyranos-5-ulose 
• 316172-37-9 2,3,4-tri-O-benzyl-5-O-methyl-1,6-anhydro-β-L-idopyranos-5-ulose 
• 316172-35-7 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 

Relevant articles and documents

Iminosugar glycoconjugates

The iminosugar conjugates according to the invention are N-alkylated 1,5-dideoxy-1,5-iminohexitol or 1,5-dideoxy-1,5-iminopentitol derivatives. The iminosugar component can be, for example, D-gluco-, L-ido-, D-galacto-, D-manno-, 2-acetamido-2-deoxy-D-gluco- or xylo-configuration. The N-substituent is a protected L-α-aminoacid derivative, showing L-lysine-like structural features. The linkage between the carbohydrate and the peptide component is not via the usual glycosidic position, but shows structural features of a very stable tertiary amine. Thus the linkage is very stable. These new compounds are synthesised by using catalytic intramolecular reductive amination of dicarbonyl sugars with partially protected amino acids. The process of intramolecular reductive amination itself is carried out using Pearlman's catalyst (Pd(OH)2/C) and H2 at ambient pressure and room temperature. The resulting accessible class of iminosugar conjugate compounds is represented by the general structure shown in Figure 4(c). The alkyl chain length parameter n can be freely chosen from n=0 upwards. Preferably n is between 0 and 10, and more preferably n is 2, 3, or 4. Residue R1 can be chosen from H, OH, or NHAc, with Ac being Acetyl. R2 can be H, OH, or NHAc. R3, R4, R5, R6 can be H or OH. R7 and R8 can be H, CH2OH CH3, COQH, or COOR with R being Alkyl or Aryl. R9 and R10 can be chosen from H, NH2, NHR, with R being a protective group, an amino acid, a peptide, or a protein. R11 can be OH, O-Alkyl, O-Aryl, NH2, N-Alkyl, N-Aryl, amino acid or peptide, connected via an amide bond.

Synthesis of D-hexos-5-uloses by novel in situ hydrolysis of epoxides derived from 6-deoxyhex-5-enopyranosides.

[reaction: see text] Epoxides derived from 2,3, 4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The prod

α-Glucosidase Inhibitors, 5.- Investigations towards a Synthesis of C1-Branched Cyclitols from D-Glucose

The glucose derivatives 1 and 2 were transformed by Ferrier rearrangement as one of the reaction steps into the cyclitol derivatives 3a,b and 4a,b, respectively.The attachment of a functional C1-side chain at the carbonyl group was tested with