(4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one

Base Information

• Chemical Name: (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one
• CAS No.: 1403757-81-2
• Molecular Formula: C₄₃H₅₁N₅O₆Si
• Molecular Weight: 761.993

Synonyms:(4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one

Chemical Property of (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one

There total 19 articles about (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one 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: 83.0%

(1S,2R,3R,4S,5S)-4-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-3-((S)-1-hydroxyethyl)-3-(4-methoxybenzylamino)-2-methyl-5-(3-(prop-1-en-2-yl)phenylamino)cyclopentane-1,2-diol (1403757-80-1) + trichloromethyl chloroformate (503-38-8) → (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one (1403757-81-2)

Guidance literature:

With pyrographite; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo301638z

Reference yield:

L-threonine → (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one (1403757-81-2)

Guidance literature:

Multi-step reaction with 24 steps

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

2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

4: diisobutylaluminium hydride / dichloromethane / -78 °C

5: methylmagnesium bromide / diethyl ether / 0 °C

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

7: ozone / dichloromethane / -78 °C

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

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

10: dihydrogen peroxide; sodium hydroxide / methanol; dichloromethane / 0 °C

11: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; dichloromethane / 0 °C

12: pyridine / -78 - 0 °C

13: tetrabutylammoniun azide / toluene / 20 °C

14: trifluoroacetic acid / acetonitrile; water / 0 - 20 °C

15: Dess-Martin periodane / dichloromethane / 0 - 20 °C

16: tetrahydrofuran / -78 °C

17: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

18: zinc trifluoromethanesulfonate; acetic acid / 80 °C

19: potassium carbonate / methanol / 20 °C

20: triethylamine; dmap / 0 - 20 °C

21: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C

22: ytterbium(III) triflate / toluene / 80 °C

23: sodium cyanoborohydride; acetic acid / toluene / 12 h / 40 °C / Inert atmosphere

24: pyrographite; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; thionyl chloride; oxalyl dichloride; trifluoromethylsulfonic anhydride; cerium(III) chloride heptahydrate; methylmagnesium bromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; tetrabutylammoniun azide; titanium tetrachloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; pyrographite; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetyl chloride; sodium hydroxide; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo301638z

Reference yield:

C39H43NO6Si → (4S,5R,6R,7S,8S,9S)-9-azido-7-((tert-butyldiphenylsilyloxy)-methyl)-6,7-dihydroxy-1-(4-methoxybenzyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]nonan-2-one (1403757-81-2)

Guidance literature:

Multi-step reaction with 22 steps

1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

2: diisobutylaluminium hydride / dichloromethane / -78 °C

3: methylmagnesium bromide / diethyl ether / 0 °C

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

5: ozone / dichloromethane / -78 °C

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

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

8: dihydrogen peroxide; sodium hydroxide / methanol; dichloromethane / 0 °C

9: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; dichloromethane / 0 °C

10: pyridine / -78 - 0 °C

11: tetrabutylammoniun azide / toluene / 20 °C

12: trifluoroacetic acid / acetonitrile; water / 0 - 20 °C

13: Dess-Martin periodane / dichloromethane / 0 - 20 °C

14: tetrahydrofuran / -78 °C

15: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

16: zinc trifluoromethanesulfonate; acetic acid / 80 °C

17: potassium carbonate / methanol / 20 °C

18: triethylamine; dmap / 0 - 20 °C

19: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C

20: ytterbium(III) triflate / toluene / 80 °C

21: sodium cyanoborohydride; acetic acid / toluene / 12 h / 40 °C / Inert atmosphere

22: pyrographite; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; chloro-trimethyl-silane; oxalyl dichloride; trifluoromethylsulfonic anhydride; cerium(III) chloride heptahydrate; methylmagnesium bromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; tetrabutylammoniun azide; titanium tetrachloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; pyrographite; Dess-Martin periodane; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetyl chloride; sodium hydroxide; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo301638z

upstream raw materials:

(1S,2R,3R,4S,5S)-4-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-3-((S)-1-hydroxyethyl)-3-(4-methoxybenzylamino)-2-methyl-5-(3-(prop-1-en-2-yl)phenylamino)cyclopentane-1,2-diol

trichloromethyl chloroformate

C₄₅H₅₇NO₆Si₂

C₃₉H₅₅NO₅Si₂

Downstream raw materials:

C₂₀H₃₀N₆O₆

de-6-MSA-pactamycate

(S)-1-((1R,2R,3S,4S,5S)-1-amino-5-azido-3-((tertbutyldiphenylsilyloxy)methyl)-2,3-dihydroxy-2-methyl-4-(3-(prop-1-en-2-yl)phenylamino)cyclopentyl)ethyl dimethylcarbamate

(1S,5R,6S,7S,8R)-6-azido-1-((tert-butyldiphenylsilyloxy)-methyl)-8-hydroxy-5-((S)-1-hydroxyethyl)-8-methyl-7-(3-(prop-1-en-2-yl)phenylamino)-2-oxa-4-azabicyclo[3.2.1]octan-3-one

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