tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate
• CAS No.: 1346507-75-2
• Molecular Formula: C₅₅H₉₁N₇O₂₃S
• Molecular Weight: 1250.43

Synonyms:tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate

Chemical Property of tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate

There total 9 articles about tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate 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: 38.0%

(4R,5S)-tert-butyl 4-(aminomethyl)-5-((1R,2S,3S,4R,5S)-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxy-5-(tert-butoxycarbonylamino)-4-((2R3R,6S)-3-(tert-butoxycarbonylamino)-6-((tert-butoxycarbonylamino)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylate + solketal tosylate (23737-51-1,7305-59-1) → tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate (1346507-75-2)

Guidance literature:

(4R,5S)-tert-butyl 4-(aminomethyl)-5-((1R,2S,3S,4R,5S)-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxy-5-(tert-butoxycarbonylamino)-4-((2R₃R,6S)-3-(tert-butoxycarbonylamino)-6-((tert-butoxycarbonylamino)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; at -60 - 20 ℃;

solketal tosylate; potassium iodide; In N,N-dimethyl-formamide; at 100 ℃; for 72h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate (1346507-75-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C

2.1: sodium dithionite; water; sodium hydroxide / ethanol / 2 h / 70 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran / 18 h / 0 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / -60 - 20 °C

4.2: 72 h / 100 °C

With sodium dithionite; water; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

Reference yield:

Gentamicin C1a (26098-04-4) → tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate (1346507-75-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

1.2: 18 h / 20 °C

1.3: 0.5 h

2.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

2.2: 18 h / 20 °C

3.1: dimethyl sulfoxide / 1 h / 20 °C

4.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 20 °C

4.2: 18 h / 20 °C

4.3: 4 h

5.1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C

6.1: sodium dithionite; water; sodium hydroxide / ethanol / 2 h / 70 °C

7.1: sodium hydrogencarbonate / tetrahydrofuran / 18 h / 0 - 20 °C

8.1: sodium hydride / N,N-dimethyl-formamide / -60 - 20 °C

8.2: 72 h / 100 °C

With 1-hydroxy-pyrrolidine-2,5-dione; sodium dithionite; water; zinc(II) acetate dihydrate; sodium hydride; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl (2R,3R,6S)-6-(aminomethyl)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-4-((methyl)tert-butoxycarbonylamino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-4-((S)-4-(tert-butoxycarbonylamino)-2-hydroxybutanamido)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-3-ylcarbamate

2-Nitrobenzenesulfonyl chloride

solketal tosylate

Gentamicin C1a

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