Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside
• CAS No.: 4141-45-1
• Molecular Formula: C18H22O8
• Molecular Weight: 366.368
• Hs Code.: 2938909090
• NSC Number: 185307,92307,281902,35901
• DSSTox Substance ID: DTXSID60935006
• ChEMBL ID: CHEMBL1867720
• Mol file: 4141-45-1.mol

Synonyms:Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside;MLS002607941;(7-acetyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl) acetate;4141-45-1;Methyl-4,6-di-O-benzylidene-2,3-di-O-acetyl-alpha-D-glucopyranoside;Methyl-4,6-di-O-benzylidene-2,3-di-O-acetyl-alpha-D-mannopyranoside;6748-84-1;NSC92307;6752-75-6;Methyl 2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranoside;CHEMBL1867720;DTXSID60935006;QOKXXIQSHLLVPF-UHFFFAOYSA-N;HMS3078E06;NSC35901;NSC-35901;NSC-92307;NSC185307;NSC281902;NSC-185307;NSC-281902;SMR001526702;Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside #;Methyl-4,6-di-O-benzylidene-2,3-di-O-acetyl-alpha-D-galactopyranoside;Acetic acid, 7-acetoxy-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside

Chemical Property:

• Melting Point: 108-109 °C
• Boiling Point: 466.5 °C at 760 mmHg
• Flash Point: 204.2 °C
• Density: 1.29 g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 366.13146766
• Heavy Atom Count: 26
• Complexity: 503

Purity/Quality:

99% ^*data from raw suppliers

METHYL-2,3-DI-O-ACETYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2C(COC(O2)C3=CC=CC=C3)OC(C1OC(=O)C)OC

Technology Process of Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside

There total 37 articles about Methyl 2,3-di-O-acetyl-4,6-O-benzylidenehexopyranoside 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: 100.0%

acetic anhydride (108-24-7) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside (2774-22-3,4141-45-1,6748-84-1,6752-75-6,15451-81-7,20750-01-0,35311-30-9,56687-82-2,59121-47-0,72813-11-7,76333-82-9,112968-15-7,130464-34-5)

Guidance literature:

With pyridine; for 2h;

DOI:10.1016/S0040-4020(02)00684-1

Reference yield: 97.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + acetic anhydride (108-24-7) → methyl-4,6-O-benzylidene-2,3-diacetyl-α-D-glucopyranoside (4141-45-1)

Guidance literature:

With erbium(III) triflate; at 20 ℃; for 0.25h;

DOI:10.1039/b511314h

Reference yield: 95.0%

acetic anhydride (108-24-7) + methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → 2,3-O-diacetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside (2774-22-3,4141-45-1,6748-84-1,6752-75-6,15451-81-7,20750-01-0,35311-30-9,56687-82-2,59121-47-0,72813-11-7,76333-82-9,112968-15-7,130464-34-5)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 90 ℃; for 8h; Sonication; Inert atmosphere;

DOI:10.1039/c2ob25452b

upstream raw materials:

pyridine

acetic anhydride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

acetyl chloride

Downstream raw materials:

methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside

methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-glucopyranoside

Refernces

• 1、 Maki, Yuta,Kajihara, Yasuhiro,Nomura, Kota,Okamoto, Ryo,Izumi, Masayuki,Mizutani, Yasuhisa. "Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group". . p. 15849 - 15856. Retrieved 2021/01/18.
• 2、 Ren, Bo,Gan, Lu,Zhang, Li,Yan, Ningning,Dong, Hai. "Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols". supporting information. p. 5591 - 5597. Retrieved 2018/08/17.