Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside
• CAS No.: 25577-40-6
• Molecular Formula: C16H20 O7
• Molecular Weight: 324.331
• Mol file: 25577-40-6.mol

Synonyms:Glucopyranoside,methyl 4,6-O-benzylidene-, 2-acetate (7CI); Glucopyranoside, methyl4,6-O-benzylidene-, 2-acetate, a-D- (8CI); a-D-Glucopyranoside,methyl 4,6-O-benzylidene-, 2-acetate (6CI); Pyrano[3,2-d]-1,3-dioxin, a-D-glucopyranoside deriv.; Methyl2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside

Chemical Property of Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside

Chemical Property:

• Melting Point: 133-134 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• Boiling Point: 471.4±45.0 °C(Predicted)
• PKA: 12.49±0.70(Predicted)
• PSA: 83.45000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 0.76450

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside

There total 42 articles about Methyl 2-O-acetyl-4,6-O-benzylidene-a-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) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (2774-23-4,20750-02-1,25577-40-6,37180-49-7,37180-53-3,57538-70-2,96779-61-2,98392-36-0,107657-07-8,107657-09-0,130195-96-9,141611-58-7,144607-24-9,144607-27-2,150654-15-2,150654-16-3)

Guidance literature:

With tetrabutylammonium acetate; In acetonitrile; at 20 ℃; Time; Temperature; Reagent/catalyst; regioselective reaction;

DOI:10.1021/jo402036u

Reference yield: 81.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + acetyl chloride (75-36-5) → methyl 2-O-acetyl-4,6-O-benzylidene-α,D-glucopyranoside (25577-40-6) + methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (18031-57-7)

Guidance literature:

With potassium iodide; silver(l) oxide; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0497252

Reference yield: 81.0%

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside (2641-79-4) + acetic anhydride (108-24-7) + 4-chlorobenzaldehyde (104-88-1) + benzaldehyde (100-52-7) + 4-bromo-benzaldehyde (1122-91-4) + benzoic acid anhydride (93-97-0) → C16H19ClO7 (942044-36-2) + C21H21ClO7 (942044-37-3) + methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (2774-23-4,20750-02-1,25577-40-6,37180-49-7,37180-53-3,57538-70-2,96779-61-2,98392-36-0,107657-07-8,107657-09-0,130195-96-9,141611-58-7,144607-24-9,144607-27-2,150654-15-2,150654-16-3) + Acetic acid (2R,4aR,6S,7R,8S,8aS)-2-(4-bromo-phenyl)-8-hydroxy-6-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester + Benzoic acid (2R,4aR,6S,7R,8S,8aS)-2-(4-bromo-phenyl)-8-hydroxy-6-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside; 4-chlorobenzaldehyde; benzaldehyde; 4-bromo-benzaldehyde; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 2h; Molecular sieve; Combinatorial reaction / High throughput screening (HTS);

With triethylsilane; β-naphthaldehyde; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 5h;

acetic anhydride; benzoic acid anhydride; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethylsilyl trifluoromethanesulfonate; more than 3 stages; Product distribution / selectivity;

upstream raw materials:

methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside]

pyridine

acetyl chloride

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

Downstream raw materials:

methyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-methyl-α-D-glucopyranoside]

methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside]

methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside]

Refernces

• 1、 Eckhardt, André K.,Erb, Frederik R.,Herold, Dominik,Kind, Jonas,Niedek, Dominik,Schreiner, Peter R.,Seitz, Alexander,Thiele, Christina M.,Topp, Christopher,Wende, Raffael C.. "In Situ Switching of Site-Selectivity with Light in the Acetylation of Sugars with Azopeptide Catalysts". supporting information. . Retrieved 2020/02/04.
• 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.