2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-D]-2-oxazoline

Base Information

• Chemical Name: 2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-D]-2-oxazoline
• CAS No.: 35954-65-5
• Molecular Formula: C₁₄H₁₉NO₈
• Molecular Weight: 329.307
• Hs Code.: 2940000080
• European Community (EC) Number: 849-899-9
• DSSTox Substance ID: DTXSID70432379
• Nikkaji Number: J109.431I
• Wikidata: Q82246448
• Mol file: 35954-65-5.mol

Synonyms:35954-65-5;FR054;2-METHYL-(3,4,6-TRI-O-ACETYL-1,2-DIDEOXY-ALPHA-D-GLUCOPYRANO)-[2,1-D]-2-OXAZOLINE;[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl acetate;2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-a-D-glucopyrano)-[2,1-d]-2-oxazoline;2-Methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyrano)-2-oxazoline;(3aR,5R,6S,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate;10378-06-0;WZFQZRLQMXZMJA-KSTCHIGDSA-;DTXSID70432379;MFCD18643061;HY-124909A;BS-45745;CS-0213510;F74875;W-202489;1-O,N,N-Ethylidyne-alpha-D-glucosamine 3,4,6-triacetate;2-Methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-?-D-glucopyrano)-?2-oxazoline;2-Methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy- alpha -D-glucopyrano)- Delta 2-oxazoline;(3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[3,2-d]oxazole-6,7-diyl diacetate;(3aR,5R,6S,7R,7aR)-5-[(Acetyloxy)methyl]-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate;5H-Pyrano[3,2-d]oxazole-6,7-diol, 5-[(acetyloxy)methyl]-3a,6,7,7a-tetrahydro-2-methyl-, diacetate (ester), [3aR-(3a.alpha.,5.alpha.,6.beta.,7.alpha.,7a.alpha.)]-;InChI=1/C14H19NO8/c1-6-15-11-13(22-9(4)18)12(21-8(3)17)10(5-19-7(2)16)23-14(11)20-6/h10-14H,5H2,1-4H3/t10-,11-,12-,13-,14+/m1/s1

Chemical Property of 2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-D]-2-oxazoline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 654.236°C at 760 mmHg
• PKA: 3.69±0.70(Predicted)
• Flash Point: 349.469°C
• PSA: 109.72000
• Density: 1.605g/cm³
• LogP: -0.60940
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 329.11106656
• Heavy Atom Count: 23
• Complexity: 531

Purity/Quality:

99%, ^*data from raw suppliers

2-Methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyrano)-?2-oxazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2C(C(C(OC2O1)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC1=N[C@@H]2[C@H]([C@@H]([C@H](O[C@@H]2O1)COC(=O)C)OC(=O)C)OC(=O)C
• Uses: 2-Methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyrano)-?2-oxazoline (cas# 35954-65-5) is a compound useful in organic synthesis. It can be used as an insecticide and miticide.

Technology Process of 2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-D]-2-oxazoline

There total 82 articles about 2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-D]-2-oxazoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

Benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid (53765-90-5) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester (171973-78-7) → Benzyl-6-O-acetyl-2,3,4,6-tri-O-benzyl-α-D-galactopyranosid (53765-91-6) + 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-((2R,3S,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 5 ℃;

DOI:10.1016/00404-0399(50)14068-

Reference yield: 87.0%

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) + phenol (108-95-2,27073-41-2) → 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) + 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose (13089-21-9)

Guidance literature:

With tin(II) trifluoromethanesulfonate; 4 A molecular sieve; tetramethylurea; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96690-5

Reference yield: 86.0%

methanol (67-56-1) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) + methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside (2771-48-4)

Guidance literature:

With tin(II) trifluoromethanesulfonate; 4 A molecular sieve; tetramethylurea; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96690-5

upstream raw materials:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

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

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

isopropyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

methyl 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside

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

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

Refernces

ω-AMINOALKYL β-GLYCOSIDES OF N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE, AND THEIR CONJUGATES WITH MENINGOCOCCAL GROUP C POLYSACCHARIDE

10.1016/0008-6215(83)88218-4

The research focuses on the synthesis of w-aminoalkyl β-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) and their conjugates with meningococcal group C polysaccharide, aiming to enhance the immunogenicity of the polysaccharide antigen. Key chemicals involved in the study include 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline, 6-(benzyloxycarbonylamino)-1-hexanol, L-alanyl-D-isoglutamine benzyl ester hydrochloride, and N-hydroxysuccinimide. The researchers synthesized the 6-aminohexyl β-glycoside of MDP and its spacer-arm-linked analog (3.8 nm) and coupled these with meningococcal group C polysaccharide. The resulting conjugates exhibited enhanced antigenicity in vitro but did not show enhanced immunogenicity in vivo.

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