N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 805245-09-4
• Molecular Formula: C₃₆H₅₉NO₆Si₃
• Molecular Weight: 686.124
• Mol file: 805245-09-4.mol

Synonyms:

Chemical Property of N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide

There total 4 articles about N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-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:

1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose (336130-11-1) → N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide (805245-09-4)

Guidance literature:

Multi-step reaction with 4 steps

1: PhI(OAc)2; n-Bu₄NN₃

2: aq. Hg(OCOCF₃)2 / tetrahydrofuran

3: PCC; NaOAc / CH₂Cl₂

4: Ra-Ni / tetrahydrofuran

With [bis(acetoxy)iodo]benzene; sodium acetate; mercury(II) trifluoroacetate; tetrabutylammoniun azide; pyridinium chlorochromate; Ra-Ni; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.09.091

Reference yield:

3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-ol → N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide (805245-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: PCC; NaOAc / CH₂Cl₂

2: Ra-Ni / tetrahydrofuran

With sodium acetate; pyridinium chlorochromate; Ra-Ni; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.09.091

Reference yield:

3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenylselanyl-tetrahydro-pyran → N-[4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide (805245-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Hg(OCOCF₃)2 / tetrahydrofuran

2: PCC; NaOAc / CH₂Cl₂

3: Ra-Ni / tetrahydrofuran

With sodium acetate; mercury(II) trifluoroacetate; pyridinium chlorochromate; Ra-Ni; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.09.091

upstream raw materials:

acetic anhydride

2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

Downstream raw materials:

[6,7-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-pyrano[3,2-d]thiazol-3a-yl]-acetic acid ethyl ester