Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside
• CAS No.: 3162-96-7
• Molecular Formula: C14H18O6
• Molecular Weight: 282.293
• Hs Code.: 29400090
• European Community (EC) Number: 221-615-2
• DSSTox Substance ID: DTXSID20953584
• Nikkaji Number: J217.318B
• Mol file: 3162-96-7.mol

Synonyms:3162-96-7;Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside;(4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;Methyl 4,6-O-benzylidene-a-D-glucopyranoside;Methyl 4,6-O-benzylidene-|A-D-glucopyranoside;MFCD00006819;(+)-(4,6-O-Benzylidene)methyl-alpha-D-glucopyranoside;Methyl 4,6-O-benzylidenehexopyranoside #;SCHEMBL37187;Glucopyranoside, methyl 4,6-O-benzylidene-, .alpha.-D-;DTXSID20953584;VVSWDMJYIDBTMV-BTZLDLHRSA-N;.alpha.-D-Glucopyranoside, methyl 4,6-O-(phenylmethylene)-;AMY24716;AKOS016010174;CS-W012263;HY-W011547;AS-10213;4,6-Benzylidene-.alpha.-methyl-D-glucoside;M1125;NS00046172;Methyl 4,6-O-Benzylidene-?-D-glucopyranoside;D70544;Methyl-4,6-O-benzylidene-.alpha. D-glucoside;Methyl 4,6-O-benzylidene-.alpha.-D-glucopyranoside;W-202306;(+)-(4,6-O-Benzylidene)methyl-?-D-glucopyranoside;(+)-Methyl-4,6-O-benzylidene-.alpha.-D-glucopyranoside;methyl 4 pound not6-O-benzylidene-|A-D-glucopyranoside;(+)-(4,6-O-Benzylidene)methyl- alpha -D-glucopyranoside;(+)-(4,6-O-Benzylidene)methyl-.alpha.-D-glucopyranoside;(+)-(4,6-O-Benzylidene)methyl-alpha-D-glucopyranoside, 97%

Chemical Property of Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 9.45E-10mmHg at 25°C
• Melting Point: 164-167 °C
• Refractive Index: 105 ° (C=2, MeOH)
• Boiling Point: 473 °C at 760 mmHg
• PKA: 12.79±0.70(Predicted)
• Flash Point: 239.8 °C
• PSA: 77.38000
• Density: 1.36 g/cm³
• LogP: 0.19370
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform, DMF, DMSO, Ethyl Acetate, Methanol
• Water Solubility.: It is soluble in water, acetone, benzene, ethyl ether
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 282.11033829
• Heavy Atom Count: 20
• Complexity: 319

Purity/Quality:

98.0%min ^*data from raw suppliers

Methyl 4,6-O-benzylidene-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 22-24/25-45-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@H]2[C@H](O1)COC(O2)C3=CC=CC=C3)O)O
• Uses: Methyl 4,6-O-Benzylidene-α-D-glucopyranoside is a derivative of methyl α-D-glucopyranoside tested for in vitro antibacterial activity. Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, is used as a chiral building block and important intermediate in the preparation of different sugars. It is also used as an intermediate in chemical, pharmaceutical intermediate, pharmaceutical research and reagent.

Technology Process of Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside

There total 112 articles about Methyl 4,6-O-benzylidene-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: 100.0%

(diethoxymethyl)benzene (774-48-1) + methyl-alpha-D-glucopyranoside (97-30-3) → 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7)

Guidance literature:

With camphor-10-sulfonic acid; In chloroform; Reflux;

DOI:10.1002/anie.201804602

Reference yield: 99.0%

4-Acetoxy-2,2-dimethyl-butyric acid (2R,4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.03.099

Reference yield: 98.0%

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) → 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7)

Guidance literature:

With methanol; potassium permanganate; trimethylsulphonium iodide; at 25 ℃; under 760.051 Torr; chemoselective reaction;

DOI:10.1039/d1ra03209g

upstream raw materials:

methyl-alpha-D-glucopyranoside

methanol

sodium methylate

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

Downstream raw materials:

Carbonic acid allyl ester (2R,4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

methyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-glucopyranoside

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

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside

Refernces

• 1、 Spanevello, Rolando A.,Saavedra, Damian D.. "Improved preparation of methyl 4,6-O-benzylidene-α-D-glucopyranoside". . p. 460 - 461. Retrieved 1999.
• 2、 Neugebauer, Dorota,Mielanczyk, Anna,Waskiewicz, Sylwia,Biela, Tadeusz. "Epoxy functionalized polymethacrylates based on various multifunctional D-glucopyranoside acetals". . p. 2483 - 2494. Retrieved 2013.
• 3、 Philips et al.. "". . p. 281,284. Retrieved 1973.
• 4、 Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj. "Me3SI-promoted chemoselective deacetylation: a general and mild protocol". . p. 19310 - 19315. Retrieved 2021/06/03.
• 5、 Cramer, Jonathan,Lakkaichi, Adem,Aliu, Butrint,Jakob, Roman P.,Klein, Sebastian,Cattaneo, Ivan,Jiang, Xiaohua,Rabbani, Said,Schwardt, Oliver,Zimmer, Gert,Ciancaglini, Matias,Abreu Mota, Tiago,Maier, Timm,Ernst, Beat. "Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2". supporting information. p. 17465 - 17478. Retrieved 2021/11/04.