22314-39-2

Basic information

• Product Name: Benzyl 2-amino-2-deoxy-β-D-glucopyranoside
• CAS NO: 22314-39-2
• Molecular Formula: C₁₃H₁₉NO₅
• Molecular Weight: 269.29366
• Mol File: 22314-39-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzyl 2-amino-2-deoxy-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-amino-2-deoxy-β-D-glucopyranoside(22314-39-2)
• EPA Substance Registry System: Benzyl 2-amino-2-deoxy-β-D-glucopyranoside(22314-39-2)

Safety Data

• Hazardous Substances Data: 22314-39-2(Hazardous Substances Data)

Upstream product

• 112146-85-7 benzyl 2-deoxy-2-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α-D-glucopyranoside 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 221687-36-1 benzyl 2-deoxy-2-[1-(1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidene)phenylmethylamino]-α-D-glucopyranoside 
• 109-73-9 N-butylamine 
• 22323-61-1 Methyl 3,4,6-tri-O-methyl-β-D-galactopyranoside 
• 110911-55-2 Methyl 2-O-allyl-3,4,6-tri-O-methyl-β-D-galactopyranoside 
• 110911-48-3 methyl-2-O-(N-imidazolylsulfonyl)-3,4,6-tri-O-methyl-β-D-galactopyranoside 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 99409-32-2 ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 

Downstream Products

• 117701-85-6 ((2S,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-benzyloxy-tetrahydro-pyran-3-yl)-trimethyl-ammonium; bromide 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 110911-57-4 benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-talopyranoside 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 791064-18-1 ((2S,3R,4R,5S,6R)-2-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid vinyl ester 
• 791064-23-8 Carbonic acid (2R,3S,4R,5R,6S)-6-benzyloxy-3,4-dihydroxy-5-vinyloxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester vinyl ester 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 174619-70-6 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-[2-((2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-amino-6-benzyloxy-tetrahydro-pyran-4-yloxy)-acetylamino]-2-acetoxymethyl-6-benzyloxy-tetrahydro-pyran-4-yl ester 
• 185607-23-2 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-benzyloxy-5-[2-((2R,4aR,6S,7R,8R,8aS)-6-benzyloxy-7-benzyloxycarbonylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-acetylamino]-tetrahydro-pyran-4-yl ester 
• 221687-36-1 benzyl 2-deoxy-2-[1-(1,3-dimethyl-2,4,6(1H,3H,5H)-trioxopyrimidin-5-ylidene)phenylmethylamino]-α-D-glucopyranoside 

Relevant articles and documents

Nickel(II) complexes with Schiff-base ligands derived from epimeric pyranose backbones as 2,3-chelators: modeling the coordination chemistry of chitosan

Two mononuclear nickel(II) complexes with Schiff-base ligands derived from the epimeric sugars glucosamine and mannosamine have been synthesized. The X-ray crystal structure reveals a distorted octahedral geometry at the nickel(II) ions with an N4/s

Design, synthesis, and antifouling activity of glucosamine-based isocyanides

Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants. Natural antifouling products obtained from marine creatures have been the subject of considerable attention due to their potent antifouling activity and low toxicity. These antifouling compounds often contain isocyano groups, which are well known to have natural antifouling properties. On the basis of our previous total synthesis of natural isocyanoterpenoids, we envisaged the installation of an isocyano functional group onto glucosamine to produce an environmentally friendly antifouling material. This paper describes an effective synthetic method for various glucosamine-based isocyanides and evaluation of their antifouling activity and toxicity against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 μg/mL).

Cross-functionalities of Bacillus deacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways

BshB, a key enzyme in bacillithiol biosynthesis, hydrolyses the acetyl group from N-acetylglucosamine malate to generate glucosamine malate. In Bacillus anthracis, BA1557 has been identified as the N-acetylglucosamine malate deacetylase (BshB); however, a