20757-53-3

Basic information

• Product Name: (3aS)-5α-[(Acetyloxy)methyl]-3aβ,6,7,7aβ-tetrahydro-2-methyl-5H-pyrano[3,2-d]oxazole-6β,7α-diol diacetate
• Synonyms: (3aS)-5α-[(Acetyloxy)methyl]-3aβ,6,7,7aβ-tetrahydro-2-methyl-5H-pyrano[3,2-d]oxazole-6β,7α-diol diacetate
• CAS NO: 20757-53-3
• Molecular Formula: C₁₄H₁₉NO₈
• Molecular Weight: 329.30256
• Mol File: 20757-53-3.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 416.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• PKA: 3.69±0.70(Predicted)
• CAS DataBase Reference: (3aS)-5α-[(Acetyloxy)methyl]-3aβ,6,7,7aβ-tetrahydro-2-methyl-5H-pyrano[3,2-d]oxazole-6β,7α-diol diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS)-5α-[(Acetyloxy)methyl]-3aβ,6,7,7aβ-tetrahydro-2-methyl-5H-pyrano[3,2-d]oxazole-6β,7α-diol diacetate(20757-53-3)
• EPA Substance Registry System: (3aS)-5α-[(Acetyloxy)methyl]-3aβ,6,7,7aβ-tetrahydro-2-methyl-5H-pyrano[3,2-d]oxazole-6β,7α-diol diacetate(20757-53-3)

Safety Data

• Hazardous Substances Data: 20757-53-3(Hazardous Substances Data)

Upstream product

• 71223-56-8 O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3068-34-6 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride 
• 10294-12-9 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 72-87-7 N-acetyl-D-mannosamine 
• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 158979-46-5 nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 79330-97-5 methyl 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 111462-60-3 methyl 3,4-di-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 75957-40-3 benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 115431-24-8 heptyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 115414-47-6 hexadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 118638-76-9 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 79184-08-0 3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose 
• 79184-08-0 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yl ester 
• 132150-14-2 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxy-hexyloxy)-tetrahydro-pyran-4-yl ester 
• 130541-93-4 benzyl O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyransoyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 95900-07-5 benzyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside 1',4-lactone 
• 92949-53-6 allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 80264-83-1 4-nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2,3-O-isopropylidene-α-D-mannopyranoside 

Relevant articles and documents

A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection

In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linkedO-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.

Dual-participation protecting group solves the anomeric stereocontrol problems in glycosylation reactions

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.