N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 143416-39-1
• Molecular Formula: C₃₀H₃₃NO₇
• Molecular Weight: 519.595
• Mol file: 143416-39-1.mol

Synonyms:

Chemical Property of N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 1 articles about N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[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:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) + p-methoxybenzyl chloride (824-94-2) → N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (143416-39-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; Yield given. Multistep reaction; 1.a) DMF, 0 deg C, 2 min, 1.b) r. t., 20 min, 2.) r. t., 1.5 h;

DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (143416-39-1) → N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:

With methanol; toluene-4-sulfonic acid; In dichloromethane; for 24h;

DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

N-[(2R,4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (143416-39-1) → benzyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (73646-11-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.1 g / MeOH, p-TsOH / CH₂Cl₂ / 24 h

2: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, r. t., 15 min, 2.) n-Bu₄NI, r. t., 4 h

3: 93 percent / ammonium cerium(IV) nitrate, H₂O / acetonitrile; CH₂Cl₂ / 0.5 h

With methanol; ammonium cerium(IV) nitrate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)81568-4

upstream raw materials:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

p-methoxybenzyl chloride

Downstream raw materials:

benzyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

N-[(2S,3R,4R,5S,6R)-2,5-Bis-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

benzyl 2-acetamido-3-O-(2-acetyl-4,6-di-O-benzyl-3-O-chloroacetyl-β-D-galactopyranosyl)-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside