N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Base Information

• Chemical Name: N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
• CAS No.: 143571-61-3
• Molecular Formula: C₄₇H₅₉NO₁₁Si
• Molecular Weight: 842.071
• Mol file: 143571-61-3.mol

Synonyms:N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Chemical Property of N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-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-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

There total 6 articles about N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-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: 88.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside (143571-60-2) → N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide (143571-61-3)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1016/S0008-6215(00)90524-X

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide (143571-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / Ag₂CO₃, AgClO₄, molecular sieves 4A / CH₂Cl₂

2: O-deacetylation

3: N₂H₄*H₂O / aq. ethanol / Heating

4: N-acetylation

5: 88 percent / p-toluenesulfonic acid

With 4 A molecular sieve; silver perchlorate; toluene-4-sulfonic acid; hydrazine hydrate; silver carbonate; In ethanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90524-X

Reference yield:

2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (143571-58-8) → N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide (143571-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / Ag₂CO₃, AgClO₄, molecular sieves 4A / CH₂Cl₂

2: O-deacetylation

3: N₂H₄*H₂O / aq. ethanol / Heating

4: N-acetylation

5: 88 percent / p-toluenesulfonic acid

With 4 A molecular sieve; silver perchlorate; toluene-4-sulfonic acid; hydrazine hydrate; silver carbonate; In ethanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90524-X

upstream raw materials:

benzaldehyde dimethyl acetal

2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

N-[(2S,3R,4R,5S,6R)-6-Benzyloxymethyl-2-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

C₇₄H₈₇NO₁₅Si