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

Base Information

• Chemical Name: (8-Acetamido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl) acetate
• CAS No.: 2484-81-3
• Molecular Formula: C₁₈H₂₃NO₇
• Molecular Weight: 365.383
• NSC Number: 156917
• DSSTox Substance ID: DTXSID00947744
• Mol file: 2484-81-3.mol

Synonyms:MLS003106447;2484-81-3;NSC156917;DTXSID00947744;NSC-156917;SMR001821350;Methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-[(1-hydroxyethylidene)amino]hexopyranoside

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

Chemical Property:

• Vapor Pressure: 3.51E-12mmHg at 25°C
• Boiling Point: 550.9°Cat760mmHg
• Flash Point: 286.9°C
• Density: 1.28g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 365.14745207
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C2C(COC(O2)C3=CC=CC=C3)OC(C1OC(=O)C)OC

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

There total 15 articles about (8-Acetamido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl) acetate 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: 15.0%

methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (99745-99-0) + acetic anhydride (108-24-7) → methyl-[O2-acetyl-3-acetylamino-O4,O6-((R)-benzylidene)-3-deoxy-α-D-glucopyranoside] (2484-81-3,4603-75-2,6748-78-3,6748-90-9,52885-42-4,110056-78-5,110534-59-3,128657-63-6,128657-64-7)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1055/s-0032-1317783

Reference yield:

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose (2880-96-8,3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2) → methyl-[O2-acetyl-3-acetylamino-O4,O6-((S)-benzylidene)-3-deoxy-α-D-idopyranoside] (2484-81-3,4603-75-2,6748-78-3,6748-90-9,52885-42-4,110056-78-5,110534-59-3,128657-63-6,128657-64-7)

Guidance literature:

With ammonium hydroxide; at 120 ℃; Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

DOI:10.1021/ja01241a003 DOI:10.1039/jr9600003392

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl-[O2-acetyl-3-acetylamino-O4,O6-((R)-benzylidene)-3-deoxy-α-D-glucopyranoside] (2484-81-3,4603-75-2,6748-78-3,6748-90-9,52885-42-4,110056-78-5,110534-59-3,128657-63-6,128657-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium periodate / water; methanol / 20 h / 5 - 20 °C / Darkness

2: water / 85 °C

3: platinum(IV) oxide; hydrogen / methanol

4: pyridine / 20 °C

With pyridine; platinum(IV) oxide; sodium periodate; hydrogen; In methanol; water;

DOI:10.1055/s-0032-1317783

upstream raw materials:

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

acetic anhydride

methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose

Downstream raw materials:

Methyl-(3-acetamino-3-deoxy-2,4,6-tri-O-acetyl-α-D-glucopyranosid)

kanosamine

methyl 3-acetamido-2-O-acetyl-3-deoxy-6-O-tosyl-α-D-glucopyranoside

(1S,2R,8S,8aR)-1,2,8-tris(benzyloxy)-octahydro-5-indolizinone