8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane

Base Information

• Chemical Name: 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane
• CAS No.: 211430-42-1
• Molecular Formula: C₃₂H₄₇NO₈SSi
• Molecular Weight: 633.879
• Mol file: 211430-42-1.mol

Synonyms:8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane

Chemical Property of 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane

There total 6 articles about 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane 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: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Toluene-4-sulfonic acid 3-(8-benzyloxycarbonylamino-1,4-dioxa-spiro[4.5]dec-8-yl)-2-hydroxy-propyl ester (159638-81-0) → 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane (211430-42-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h;

DOI:10.1016/S0040-4020(02)00436-2

Reference yield:

cyclohexanone-4-carboxylic acid ethyleneacetal (66500-55-8) → 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane (211430-42-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 78 percent / tetrahydrofuran; hexane / 2 h / 20 °C

2.1: diphenylphosphoryl azide; triethylamine / benzene / 0.5 h / Heating

2.2: 65 percent / benzene / 5 h / Heating

3.1: 94 percent / osmium tetroxide; N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

4.1: 86 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 4 h / 20 °C

5.1: 92 percent / imidazole / dimethylformamide / 4.5 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; diphenylphosphoranyl azide; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; hexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(02)00436-2

Reference yield:

8-(2'-propenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid (159638-73-0) → 8-(2'-tert-butyldimethylsilyloxy-3'-tosyloxypropyl)-8-phenylmethoxycarbonylamino-1,4-dioxaspiro[4.5]decane (211430-42-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diphenylphosphoryl azide; triethylamine / benzene / 0.5 h / Heating

1.2: 65 percent / benzene / 5 h / Heating

2.1: 94 percent / osmium tetroxide; N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3.1: 86 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 4 h / 20 °C

4.1: 92 percent / imidazole / dimethylformamide / 4.5 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; diphenylphosphoranyl azide; 4-methylmorpholine N-oxide; triethylamine; In pyridine; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(02)00436-2

upstream raw materials:

tert-butyldimethylsilyl chloride

Toluene-4-sulfonic acid 3-(8-benzyloxycarbonylamino-1,4-dioxa-spiro[4.5]dec-8-yl)-2-hydroxy-propyl ester

cyclohexanone-4-carboxylic acid ethyleneacetal

8-(2'-propenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid

Downstream raw materials:

C₂₆H₃₄N₂O₄

C₂₆H₃₆N₂O₃

Toluene-4-sulfonic acid 3-(8-amino-1,4-dioxa-spiro[4.5]dec-8-yl)-2-(tert-butyl-dimethyl-silanyloxy)-propyl ester