N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 495391-23-6
• Molecular Formula: C₃₉H₅₇N₅O₁₁Si
• Molecular Weight: 799.994
• Mol file: 495391-23-6.mol

Synonyms:N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property of N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-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,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 9 articles about N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-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: 79.0%

N-[6-[5-acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (495391-19-0) → N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (495391-23-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1016/S0040-4039(02)01753-7

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (495391-23-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / NaH; TBAI / tetrahydrofuran / Heating

2: 72 percent / Me₃N*BH₃; AlCl₃ / tetrahydrofuran

3: 67 percent / NIS; TMSOTf

4: 62 percent / NIS; TMSOTf

5: ethylene diamine / ethanol

6: methanol

7: 79 percent / DDQ / CH₂Cl₂; H₂O

With N-iodo-succinimide; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; tetra-(n-butyl)ammonium iodide; sodium hydride; ethylenediamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(02)01753-7

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → N-[(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-5-Acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (495391-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂

2: 62 percent / NIS; TMSOTf

3: ethylene diamine / ethanol

4: methanol

5: 79 percent / DDQ / CH₂Cl₂; H₂O

With 2,6-dimethylpyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; ethylenediamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(02)01753-7

upstream raw materials:

N-[6-[5-acetylamino-6-(3-azido-propoxy)-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

t-butyldimethylsiyl triflate

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside