D-Alanine,N-(cyclohexylcarbonyl)-,(10R,11E,13E,15E,18S,19R,20R,21Z)-3,4,7,8,9,10,17,18,19,20,23,24-dodecahydro-20,26-dihydroxy-10-methoxy-19,21-dimethyl-3,8-dioxo-2H-6,25-metheno-1,4-thiazino[3,2-d]azacyclotricosin-18-ylester

Base Information

• Chemical Name: D-Alanine,N-(cyclohexylcarbonyl)-,(10R,11E,13E,15E,18S,19R,20R,21Z)-3,4,7,8,9,10,17,18,19,20,23,24-dodecahydro-20,26-dihydroxy-10-methoxy-19,21-dimethyl-3,8-dioxo-2H-6,25-metheno-1,4-thiazino[3,2-d]azacyclotricosin-18-ylester
• CAS No.: 165337-97-3
• Molecular Formula: C38H51 N3 O8 S
• Molecular Weight: 709.904
• Mol file: 165337-97-3.mol

Synonyms:(+)-ThiazinotrienomycinE; Thiazinotrienomycin E

Chemical Property of D-Alanine,N-(cyclohexylcarbonyl)-,(10R,11E,13E,15E,18S,19R,20R,21Z)-3,4,7,8,9,10,17,18,19,20,23,24-dodecahydro-20,26-dihydroxy-10-methoxy-19,21-dimethyl-3,8-dioxo-2H-6,25-metheno-1,4-thiazino[3,2-d]azacyclotricosin-18-ylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Alanine,N-(cyclohexylcarbonyl)-,(10R,11E,13E,15E,18S,19R,20R,21Z)-3,4,7,8,9,10,17,18,19,20,23,24-dodecahydro-20,26-dihydroxy-10-methoxy-19,21-dimethyl-3,8-dioxo-2H-6,25-metheno-1,4-thiazino[3,2-d]azacyclotricosin-18-ylester

There total 49 articles about D-Alanine,N-(cyclohexylcarbonyl)-,(10R,11E,13E,15E,18S,19R,20R,21Z)-3,4,7,8,9,10,17,18,19,20,23,24-dodecahydro-20,26-dihydroxy-10-methoxy-19,21-dimethyl-3,8-dioxo-2H-6,25-metheno-1,4-thiazino[3,2-d]azacyclotricosin-18-ylester 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:

methyl 2-fluoro-6-methoxybenzoate (178747-79-0) → (+)-thiazinotrienomycin E (165337-97-3)

Guidance literature:

Multi-step reaction with 25 steps

1: 95 percent / NO₂BF₄

2: SnCl₂; aq. HCl

3: 60 percent / LiBEt₃H; 15-crown-5 / tetrahydrofuran

4: DMAP

5: NaI

6: 85 percent / BBr₃ / CH₂Cl₂

7: 100 percent / dimethylformamide

8: NaHMDS

9: Na/Hg

10: SiO₂ / CHCl₃

11: TBAF; AcOH / 0 °C

12: 88 percent / TBAF

13: Py-SO₃ / dimethylsulfoxide

14: aq. NaClO₂

15: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

16: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

17: 90 percent / camphorsulfonic acid / methanol / 0.25 h

18: DMAP / tetrahydrofuran / -78 °C

19: Et₂NH / tetrahydrofuran

20: BOP; Et₃N / tetrahydrofuran

21: aq. HCl / tetrahydrofuran

With hydrogenchloride; dmap; sodium chlorite; sodium amalgam; nitronium tetrafluoborate; 15-crown-5; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; boron tribromide; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; acetic acid; diethylamine; triethylamine; sodium iodide; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 17: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

Reference yield:

2-fluoro-6-methoxy-3,5-dinitro-benzoic acid methyl ester (251089-58-4) → (+)-thiazinotrienomycin E (165337-97-3)

Guidance literature:

Multi-step reaction with 24 steps

1: SnCl₂; aq. HCl

2: 60 percent / LiBEt₃H; 15-crown-5 / tetrahydrofuran

3: DMAP

4: NaI

5: 85 percent / BBr₃ / CH₂Cl₂

6: 100 percent / dimethylformamide

7: NaHMDS

8: Na/Hg

9: SiO₂ / CHCl₃

10: TBAF; AcOH / 0 °C

11: 88 percent / TBAF

12: Py-SO₃ / dimethylsulfoxide

13: aq. NaClO₂

14: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

15: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

16: 90 percent / camphorsulfonic acid / methanol / 0.25 h

17: DMAP / tetrahydrofuran / -78 °C

18: Et₂NH / tetrahydrofuran

19: BOP; Et₃N / tetrahydrofuran

20: aq. HCl / tetrahydrofuran

With hydrogenchloride; dmap; sodium chlorite; sodium amalgam; 15-crown-5; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; boron tribromide; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; acetic acid; diethylamine; triethylamine; sodium iodide; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 16: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

Reference yield:

6-amino-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-8-carboxylic acid methyl ester (286372-24-5) → (+)-thiazinotrienomycin E (165337-97-3)

Guidance literature:

Multi-step reaction with 22 steps

1: 60 percent / LiBEt₃H; 15-crown-5 / tetrahydrofuran

2: DMAP

3: NaI

4: 85 percent / BBr₃ / CH₂Cl₂

5: 100 percent / dimethylformamide

6: NaHMDS

7: Na/Hg

8: SiO₂ / CHCl₃

9: TBAF; AcOH / 0 °C

10: 88 percent / TBAF

11: Py-SO₃ / dimethylsulfoxide

12: aq. NaClO₂

13: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

14: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

15: 90 percent / camphorsulfonic acid / methanol / 0.25 h

16: DMAP / tetrahydrofuran / -78 °C

17: Et₂NH / tetrahydrofuran

18: BOP; Et₃N / tetrahydrofuran

19: aq. HCl / tetrahydrofuran

With hydrogenchloride; dmap; sodium chlorite; sodium amalgam; 15-crown-5; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; boron tribromide; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; acetic acid; diethylamine; triethylamine; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 14: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

upstream raw materials:

Fmoc-D-alanine anhydride

(+)-thiazinotrienomycinol

Cyclohexanecarboxylic acid

C₃₈H₅₁N₃SO₈C₂H₄O

Downstream raw materials:

(6E,8E,10E,16Z)-(5R,13S,14S,15R)-13,15,28-Trihydroxy-5-methoxy-14,16-dimethyl-22-thia-2,25-diaza-tricyclo[18.7.1.0^21,26]octacosa-1⁽²⁷⁾,6,8,10,16,20⁽²⁸⁾,21⁽²⁶⁾-heptaene-3,24-dione

Refernces

• 1、 Smith III, Amos B.,Wan, Zehong. "Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E". . p. 3738 - 3753. Retrieved 2007/10/03.