METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE

Base Information

• Chemical Name: METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE
• CAS No.: 3150-15-0
• Molecular Formula: C14H16O5
• Molecular Weight: 264.278
• Hs Code.: 29329990
• European Community (EC) Number: 221-582-4
• DSSTox Substance ID: DTXSID601180045
• Nikkaji Number: J217.303D
• Mol file: 3150-15-0.mol

Synonyms:Methyl 2,3-anhydro-4,6-O-(benzylidene)-alpha-allo-D-pyranoside;

Chemical Property of METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 201-202℃
• Refractive Index: 1.577
• Boiling Point: 391.011 °C at 760 mmHg
• Flash Point: 165.408 °C
• PSA: 49.45000
• Density: 1.322 g/cm³
• LogP: 1.23930
• Storage Temp.: 2-8°C
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1C2C(O2)C3C(O1)COC(O3)C4=CC=CC=C4
• Isomeric SMILES: CO[C@@H]1[C@H]2[C@H](O2)[C@H]3[C@H](O1)COC(O3)C4=CC=CC=C4

Technology Process of METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE

There total 95 articles about METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE 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