(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

Base Information

• Chemical Name: (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
• CAS No.: 1403757-80-1
• Molecular Formula: C₄₂H₅₃N₅O₅Si
• Molecular Weight: 735.999

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (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

There total 19 articles about (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 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: 77.0%

C42H49N5O5Si (1295471-25-8) → (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)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In toluene; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo301638z

Reference yield:

L-threonine → (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)

Guidance literature:

Multi-step reaction with 23 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

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; 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 → (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)

Guidance literature:

Multi-step reaction with 21 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

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; 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:

C₄₅H₅₇NO₆Si₂

C₃₉H₅₅NO₅Si₂

C₃₈H₅₁NO₆Si₂

C₃₈H₅₁NO₆Si₂

Downstream raw materials:

(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

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

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