Methyl 2,3,6-Tri-O-acetyl-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3,6-Tri-O-acetyl-alpha-D-glucopyranoside
• CAS No.: 18031-51-1
• Molecular Formula: C13H20 O9
• Molecular Weight: 320.296
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID80453196
• Nikkaji Number: J783.013K
• Wikidata: Q82274271
• Mol file: 18031-51-1.mol

Synonyms:18031-51-1;Methyl 2,3,6-tri-O-acetyl-a-D-glucopyranoside;Methyl 2,3,6-Tri-O-acetyl-alpha-D-glucopyranoside;[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-3-hydroxy-6-methoxyoxan-2-yl]methyl acetate;alpha-D-Glucopyranoside, methyl, 2,3,6-triacetate;SCHEMBL8824642;DTXSID80453196;AKOS027447476;Methyl 2,3,6-Tri-O-acetyl-?-D-glucopyranoside;1-O-Methyl-alpha-D-glucopyranose 2,3,6-triacetate;Methyl 2,3,6-tri-O-acetyl-alpha-D-glucopyranoside?

Chemical Property of Methyl 2,3,6-Tri-O-acetyl-alpha-D-glucopyranoside

Chemical Property:

• PSA: 117.59000
• LogP: -0.85490
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 320.11073221
• Heavy Atom Count: 22
• Complexity: 422

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl2,3,6-Tri-O-acetyl-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC)OC(=O)C)OC(=O)C)O
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC)OC(=O)C)OC(=O)C)O
• Uses: Methyl 2,3,6-Tri-O-acetyl-α-D-glucopyranoside (cas# 18031-51-1) is a compound useful in organic synthesis.

Technology Process of Methyl 2,3,6-Tri-O-acetyl-alpha-D-glucopyranoside

There total 26 articles about Methyl 2,3,6-Tri-O-acetyl-alpha-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%

acetic anhydride (108-24-7) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside (18031-51-1)

Guidance literature:

methyl-alpha-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; for 2h; Heating;

acetic anhydride; In acetonitrile; at 20 ℃;

DOI:10.1021/jo0620821

Reference yield: 90.0%

acetic anhydride (108-24-7) + methyl 2,3-di-O-acetyl-α-D-glucopyranoside (29868-42-6) → methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside (18031-51-1)

Guidance literature:

With 4 A molecular sieve; at 0 ℃; for 5h;

DOI:10.1016/S0040-4039(03)01072-4

Reference yield: 89.0%

methyl 2,3,6-tri-O-acetyl-4-O-diphenylmethyl-α-D-glucopyranoside (81712-51-8) → Diphenylmethane (101-81-5) + methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside (18031-51-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h; under 760 Torr;

DOI:10.1016/S0008-6215(00)88058-1

upstream raw materials:

methyl 2,3-di-O-acetyl-α-D-glucopyranoside

(E)-3-Ureido-but-2-enoic acid ethyl ester

methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose

methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside

Downstream raw materials:

C₂₃H₃₀NO₁₂P

methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-α-L-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-β-L-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

Refernces

• 1、 Liu,H.W.,Nakanishi,K.. "-". . p. 1178. Retrieved 1982.
• 2、 Fan, Qiuhua,Jia, Peijing,McCarty, Bethany J.,Tang, Weiping,Wen, Peng. "Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars". . . Retrieved 2022/01/13.
• 3、 Yan, Ming-Chung,Chen, Yeng-Nan,Wu, Huan-Ting,Lin, Chang-Ching,Chen, Chien-Tien,Lin, Chun-Cheng. "Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst". . p. 299 - 302. Retrieved 2007/10/03.