(4Ar,6S,7S,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Base Information

• Chemical Name: (4Ar,6S,7S,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS No.: 65530-26-9
• Molecular Formula: C₁₄H₁₈O₆
• Molecular Weight: 282.293
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID40482169
• Nikkaji Number: J1.340.658H
• Mol file: 65530-26-9.mol

Synonyms:65530-26-9;(4Ar,6S,7S,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;Methyl-4,6-O-benzyliden-alpha-D-mannopyranoside;CTK8G1077;DTXSID40482169

Chemical Property of (4Ar,6S,7S,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property:

• PSA: 77.38000
• LogP: 0.19370
• 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%,99%, ^*data from raw suppliers

4,6-O-BENZYLIDENE-1-O-METHYL-BETA-D-GALACTOSIDE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of (4Ar,6S,7S,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

There total 35 articles about (4Ar,6S,7S,8S,8aS)-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

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