N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

Base Information

• Chemical Name: N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide
• CAS No.: 6619-04-1
• Molecular Formula: C16H21 N O6
• Molecular Weight: 323.346
• Hs Code.: 9999999999
• NSC Number: 212135,75588
• DSSTox Substance ID: DTXSID90291445,DTXSID40984678
• ChEMBL ID: CHEMBL1870280
• Mol file: 6619-04-1.mol

Synonyms:MLS002693953;17327-07-0;N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide;6619-04-1;Methyl2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside;alpha-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-;NSC75588;CHEMBL1870280;DTXSID40984678;DTXSID90291445;NSC-75588;NSC212135;NSC-212135;SMR001559890;FT-0671407;Methyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

Chemical Property of N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

Chemical Property:

• Vapor Pressure: 2.9E-14mmHg at 25°C
• Boiling Point: 579.4°Cat760mmHg
• Flash Point: 304.2°C
• PSA: 86.25000
• Density: 1.3g/cm³
• LogP: 0.72840
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 323.13688739
• Heavy Atom Count: 23
• Complexity: 413

Purity/Quality:

95% ^*data from raw suppliers

Methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1OC)O

Technology Process of N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

There total 26 articles about N-(8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 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: 99.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl 2-acetylamido-2-deoxy-D-glucoside (6082-04-8) → methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 10h; under 150.015 Torr;

DOI:10.1002/adsc.201100735

Reference yield: 85.7%

methyl N-acetyl-D-glucosamine (3055-46-7,3946-01-8,5627-24-7,6082-04-8,6082-22-0,17327-09-2,22256-76-4,32087-35-7,32087-36-8,95341-97-2,114029-61-7,114612-10-1,114612-13-4,116559-74-1) + benzaldehyde (100-52-7) → N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (6619-04-1)

Guidance literature:

With zinc(II) chloride; for 24h;

DOI:10.1016/0008-6215(83)84058-0

Reference yield: 85.0%

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside (100638-83-3) → methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside (93453-17-9) + methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

upstream raw materials:

2-acetylamino-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-D-glucose

dimethyl sulfate

benzaldehyde

methyl N-acetyl-β-D-glucosaminide

Downstream raw materials:

methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl 2-acetamido-4,6-O-benzylidene-3-O-mesyl-2-deoxy-α-D-glucopyranoside

methyl-[2-acetylamino-O⁴,O⁶-((Ξ)-benzylidene)-O³-(toluene-4-sulfonyl)-2-deoxy-α-D-glucopyranoside]

methyl-[2-acetylamino-O⁴,O⁶-((Ξ)-benzylidene)-O³-methyl-2-deoxy-α-D-glucopyranoside]