6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Base Information

• Chemical Name: 6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS No.: 4148-58-7
• Molecular Formula: C14H18 O6
• Molecular Weight: 282.293
• Hs Code.: 2932999099
• European Community (EC) Number: 221-615-2
• NSC Number: 170162,92312,34712,1953,1681
• Nikkaji Number: J2.293.853C
• ChEMBL ID: CHEMBL1488601
• Mol file: 4148-58-7.mol

Synonyms:3162-96-7;6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;Methyl 4,6-O-benzylidene-D-altropyranoside;Methyl 4,6-O-benzylidene-a-D-glucopyranoside;(+)-(4,6-O-Benzylidene)methyl-alpha-D-glucopyranoside;14155-23-8;5328-47-2;Altropyranoside,6-O-benzylidene-, .alpha.-D-;.alpha.-D-Altropyranoside,6-O-(phenylmethylene)-;6988-39-2;72904-85-9;METHYL4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE;MFCD00006819;6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7,8-diol;65530-26-9;Methyl 4,6-O-benzylidenehexopyranoside #;METHYL-4,6-O-BENZYLIDEN-BETA-D-GALACTOPYRANOSIDE;TimTec1_000314;Oprea1_664495;CBDivE_002430;SCHEMBL4546275;CHEMBL1488601;NSC1681;NSC1953;VVSWDMJYIDBTMV-UHFFFAOYSA-N;HMS1534O06;NSC 1681;NSC-1681;NSC-1953;NSC34712;NSC92312;EINECS 221-615-2;NSC-34712;NSC-92312;NSC170162;AKOS003238190;NSC-170162;SB47924;2-methoxy-6-phenyl-2H-3,4,5,6,7,8,4a,8a-octahydro-5,7-dioxachromene-3,4-diol;NCGC00142340-01;NCGC00142340-02;SY001543;FT-0628601;FT-0628843;FT-0656816;FT-0657247;FT-0671547;FT-0697702;methyl 4?6-O-benzylidene-?-D-glucopyranoside;Glucopyranoside,6-O-benzylidene-, .alpha.-D-;Mannopyranoside,6-O-benzylidene-, .alpha.-D-;.alpha.-D-Glucopyranoside,6-O-(phenylmethylene)-;.alpha.-D-Mannopyranoside,6-O-(phenylmethylene)-;A836683;A837666;AE-641/00618028;BRD-A61584256-001-01-5;METHYL4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE;B2705-294179;6-Methoxy-2-phenyl-hexahydropyrano[2,3-b][1,3]dioxine-7,8-diol;(2S,4aR,6R,7R,8R,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property of 6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property:

• Melting Point: 141-143°C
• PSA: 77.38000
• LogP: 0.19370
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• 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:

99%, ^*data from raw suppliers

Methyl 4,6-O-Benzylidene-a-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)O
• Uses: Methyl 4,6-O-Benzylidene-α-D-mannopyranoside and its derivative were tested for in vitro antibacterial activity.

Technology Process of 6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

There total 48 articles about 6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 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: 98.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → 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)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1021/ol030023t

Reference yield: 98.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl beta-D-galactopyranoside (1824-94-8) → methyl 4,6-O-benzylidene-β-D-galactopyranoside (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)

Guidance literature:

With sulfuric acid; In methanol; Heating;

DOI:10.1007/BF00581609

Reference yield: 94.0%

methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside (73395-15-0) → 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)

Guidance literature:

With phosphomolybdic acid; silica gel; In dichloromethane; at 20 ℃; for 2h; chemoselective reaction;

DOI:10.1002/ejoc.200800963

upstream raw materials:

methyl β-D-galactopyranoside

benzaldehyde dimethyl acetal

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

benzaldehyde

Downstream raw materials:

Methyl-4,5-O-benzyliden-2,3-carbonato-α-D-mannopyranosid

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-mannopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

Methyl 2-O-acetyl-4,6-O-(phenylmethylene)-α-D-mannopyranoside