(4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol

Base Information

• Chemical Name: (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol
• CAS No.: 1403757-63-0
• Molecular Formula: C₃₃H₃₉NO₅Si
• Molecular Weight: 557.762

Synonyms:(4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol

Chemical Property of (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol

There total 10 articles about (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol 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: 86.0%

(4S,5S,6R)-8-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4-methyl-9-oxo-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate (1403757-61-8) + methylmagnesium bromide (75-16-1) → (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol (1403757-63-0)

Guidance literature:

With (dimethylamino)trimethyltin; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 0.833333h; Inert atmosphere;

DOI:10.1021/jo301638z

Reference yield:

(4S,5R,6R,9S)-8-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4-methyl-9-(triethylsilyloxy)-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-ol (1403757-58-3) → (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol (1403757-63-0)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / acetonitrile; water / 72 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: (dimethylamino)trimethyltin / tetrahydrofuran; diethyl ether / 0.83 h / -78 - 0 °C / Inert atmosphere

With dmap; (dimethylamino)trimethyltin; Dess-Martin periodane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo301638z

Reference yield:

L-threonine → (4S,5R,6S,9R)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-diene-6,9-diol (1403757-63-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: thionyl chloride / acetonitrile / 0 - 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

4.1: diisobutylaluminium hydride / dichloromethane / -78 °C

5.1: methylmagnesium bromide / diethyl ether / 0 °C

6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C

7.1: ozone / dichloromethane / -78 °C

8.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride; chloro-trimethyl-silane / dichloromethane / 0 °C

9.1: trifluoroacetyl chloride; pyridine / dichloromethane / 20 °C

10.1: cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.17 h / 0 °C / Inert atmosphere

10.2: 1 h / 0 °C / Inert atmosphere

11.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

12.1: trifluoroacetic acid / acetonitrile; water / 72 h / 20 °C

13.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

14.1: (dimethylamino)trimethyltin / tetrahydrofuran; diethyl ether / 0.83 h / -78 - 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; dmap; chloro-trimethyl-silane; thionyl chloride; oxalyl dichloride; cerium(III) chloride heptahydrate; methylmagnesium bromide; titanium tetrachloride; (dimethylamino)trimethyltin; diisobutylaluminium hydride; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo301638z

upstream raw materials:

(4S,5R,6R,9S)-8-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4-methyl-9-(triethylsilyloxy)-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-ol

(4S,5S)-benzyl 2-(4-methoxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carboxylate

C₄₅H₅₇NO₆Si₂

C₃₉H₅₅NO₅Si₂

Downstream raw materials:

(4S,5S,6R,9S)-8-((tert-butyldiphenylsilyloxy)methyl)-9-hydroxy-2-(4-methoxyphenyl)-4,9-dimethyl-3-oxa-1-azaspiro[4.4]nona-1,7-dien-6-yl acetate

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