Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside

Base Information

• Chemical Name: Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside
• CAS No.: 173725-22-9
• Molecular Formula: C22H37NO9
• Molecular Weight: 459.53
• DSSTox Substance ID: DTXSID40585907
• Nikkaji Number: J789.536D
• Wikidata: Q72497488
• Mol file: 173725-22-9.mol

Synonyms:173725-22-9;Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside;[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-octoxyoxan-2-yl]methyl acetate;Octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside;beta-D-Glucopyranoside, octyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate;(2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(octyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate;SCHEMBL4989193;DTXSID40585907;[(2R,3S,4R,5R,6R)-3,4-BIS(ACETYLOXY)-5-ACETAMIDO-6-(OCTYLOXY)OXAN-2-YL]METHYL ACETATE;AKOS002687938;Z1801318654;Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-?-D-glucopyranoside;Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-b-D-glucopyranoside;Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl- beta -D-glucopyranoside;Octyl-2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-I(2)-D-glucopyranoside

Chemical Property of Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside

Chemical Property:

• Boiling Point: 576.195 °C at 760 mmHg
• Flash Point: 302.272 °C
• PSA: 126.46000
• Density: 1.15 g/cm³
• LogP: 2.41050
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Methanol
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 16
• Exact Mass: 459.24683176
• Heavy Atom Count: 32
• Complexity: 625

Purity/Quality:

98%Min ^*data from raw suppliers

Octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCOC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Isomeric SMILES: CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Uses: Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (cas# 173725-22-9) is a compound useful in organic synthesis.

Technology Process of Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside

There total 7 articles about Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside 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: 90.0%

octanol (111-87-5) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (173725-22-9)

Guidance literature:

With 4 A molecular sieve; iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(96)01995-8

Reference yield: 81.0%

octanol (111-87-5) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (173725-22-9)

Guidance literature:

With silica-gel-supported sulfuric acid; In 1,2-dichloro-ethane; at 110 ℃; for 0.25h; stereoselective reaction; Microwave irradiation;

DOI:10.1055/s-0029-1218304

Reference yield: 76.0%

phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside (27526-42-7) + octanol (111-87-5) → n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (173725-22-9)

Guidance literature:

With N-iodo-succinimide; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; for 4.5h; Inert atmosphere; Reflux;

DOI:10.1016/j.carres.2010.02.013

upstream raw materials:

octanol

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

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

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

Downstream raw materials:

N-((2R,4aR,6R,7R,8S,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

1-octyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-octyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine

Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Refernces

• 1、 Mandai, Santanu,Sharma, Nayan,Mukhopadhyay, Balaram. "H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions". experimental part. p. 3111 - 3114. Retrieved 2010/03/03.
• 2、 Ogawa, Seiichiro,Matsunaga, Naoki,Li, Hong,Palcic, Monica M.. "Pseudosugars, 40: Synthesis of ether- and imino-linked octyl N-acetyl- 5a'-carba-β-lactosaminides and -isolactosaminides: Acceptor substrates for α-(1→3/4)-fucosyltransferase, and enzymatic synthesis of 5a'- carbatrisaccharides". . p. 631 - 642. Retrieved 2007/10/03.