Methyl 2,3-anhydro-4,6-O-benzylidenehexopyranoside

Base Information

• Chemical Name: Methyl 2,3-anhydro-4,6-O-benzylidenehexopyranoside
• CAS No.: 3150-16-1
• Molecular Formula: C14H16 O5
• Molecular Weight: 264.278
• NSC Number: 623664,170243,170222,161077,41445,41444
• DSSTox Substance ID: DTXSID10941213
• Nikkaji Number: J3.180.307A
• ChEMBL ID: CHEMBL1863752
• Mol file: 3150-16-1.mol

Synonyms:Methyl 2,3-anhydro-4,6-O-benzylidenehexopyranoside;MLS002608315;NSC623664;19465-13-5;3150-16-1;NSC41444;EINECS 221-582-4;SCHEMBL4546279;CHEMBL1863752;DTXSID10941213;HMS3092F15;NSC41445;NSC 41444;NSC-41444;NSC-41445;NSC161077;NSC170222;NSC170243;AKOS024307001;NSC-161077;NSC-170222;NSC-170243;NSC-623664;SMR001527065;Methyl 2,6-o-benzylidene-d-mannopyranoside;D-Mannopyranoside,3-anhydro-4,6-O-(phenylmethylene)-;Mannopyranoside,3-anhydro-4,6-O-benzylidene-, .alpha.-D-;.alpha.-D-Mannopyranoside,3-anhydro-4,6-O-(phenylmethylene)-;Methyl 2,3-anhydro-4,6-O-(benzylidene)-alpha-allo-D-pyranoside;(1R,2R,4R,5S,7R)-5-methoxy-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.0^{2,4]undecane;2-methoxy-6-phenyl-1a,2,3a,4,7a,7b-hexahydrooxireno[[?]:[?]]pyrano[[?]][1,3]dioxine;53270-02-3;67226-04-4

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

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 146-147℃
• Boiling Point: 391°Cat760mmHg
• Flash Point: 165.4°C
• PSA: 49.45000
• Density: 1.32g/cm³
• LogP: 1.23930
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 264.09977361
• Heavy Atom Count: 19
• Complexity: 330

Purity/Quality:

99% ^*data from raw suppliers

METHYL-2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-MANNO-PYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C2C(O2)C3C(O1)COC(O3)C4=CC=CC=C4

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

There total 89 articles about Methyl 2,3-anhydro-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: 86.0%

4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside (129217-24-9) → methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 23 ℃; for 2h;

DOI:10.1021/jo00052a058

Reference yield: 85.0%

methyl 4,6-O-benzylidene-α-D-altropyranoside (71117-41-4) → methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8)

Guidance literature:

With sodium hydroxide; p-toluenesulfonyl chloride; benzyltriethylammonium bromide; In dichloromethane; at 25 ℃; for 0.166667h;

DOI:10.1055/s-1985-31416

Reference yield: 76.0%

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) + methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside (66537-92-6)

Guidance literature:

With p-toluenesulfonyl chloride; tetra(n-butyl)ammonium hydrogensulfate;

DOI:10.1016/0008-6215(88)80054-5

upstream raw materials:

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

methanol

sodium methylate

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

Downstream raw materials:

methyl-[O⁴,O⁶-((R)-benzylidene)-3-iodo-3-deoxy-α-D-altropyranoside]

methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

methyl-3-deoxyamino-4,6-dioxabenzylidene-α-D-altropyranose

Refernces

• 1、 B?ge, Matthias,Fowelin, Christian,Bednarski, Patrick,Heck, Jürgen. "Diaminohexopyranosides as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes". . p. 1507 - 1521. Retrieved 2015/05/13.
• 2、 -. "SACCHARIDE CONJUGATES". Paragraph 0228; 0230. . Retrieved 2014/10/04.