N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-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-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 147314-93-0
• Molecular Formula: C₂₆H₃₆N₂O₁₁
• Molecular Weight: 552.579
• Mol file: 147314-93-0.mol

Synonyms:

Chemical Property of N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-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-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-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-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-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:

benzaldehyde dimethyl acetal (1125-88-8) + allyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside (126628-25-9) → N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (147314-93-0)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1990.1611

Reference yield:

N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (147314-93-0) → N-{(2R,3R,4R,5S,6R)-5-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-allyloxy-4-benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl}-acetamide (131712-06-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 95 percent / BaO, Ba(OH)2 / dimethylformamide

With pyridine; barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1990.1611

Reference yield:

N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-allyloxy-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (147314-93-0) → C67H76N2O15 (131712-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: 95 percent / BaO, Ba(OH)2 / dimethylformamide

3: 79 percent / pyridinium p-toluolsulfonic acid / ethanol; CHCl₃ / 0.5 h / Ambient temperature

4: 58 percent / tetraethylammonium bromide, 4A molecular sieves / 1,2-dichloro-ethane; dimethylformamide

With pyridine; barium dihydroxide; 4 A molecular sieve; tetraethylammonium bromide; pyridinium p-toluenesulfonate; barium(II) oxide; In ethanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1246/cl.1990.1611

upstream raw materials:

benzaldehyde dimethyl acetal

allyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

allyl 2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside

N-{(2R,3R,4R,5S,6R)-5-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-allyloxy-4-benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-3-yl}-acetamide

C₆₇H₇₆N₂O₁₅