(4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester

Base Information

• Chemical Name: (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester
• CAS No.: 364631-66-3
• Molecular Formula: C₃₃H₄₇N₃O₆
• Molecular Weight: 581.753
• Mol file: 364631-66-3.mol

Synonyms:(4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester

Chemical Property of (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester

There total 20 articles about (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester 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: 72.0%

(4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester (364631-55-0) → (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester (364631-66-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol016336a

Reference yield:

4-benzyloxybutanal (5470-84-8) → (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester (364631-66-3)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 80 percent / tetrahydrofuran / 0 °C

2.1: 85 percent / Jones reagent / 0 °C

3.1: (R)-Alpine borane / tetrahydrofuran / -10 - 20 °C

4.1: 80 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: 90 percent / n-BuLi / tetrahydrofuran / -78 °C

6.1: 70 percent / CuBr*DMS / tetrahydrofuran / -78 - 20 °C

7.1: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

8.1: 76 percent / NaH / dimethylformamide; various solvent(s) / 5 h / 0 - 20 °C

9.1: 91 percent / diisobutylaluminium hydride / CH₂Cl₂; petroleum ether / 2 h / -78 °C

10.1: t-BuOOH; CaH₂; SiO₂ / (-)-DIPT; Ti(O-i-Pr)4 / CH₂Cl₂; toluene / 72 h / -20 °C

11.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 - 20 °C

12.1: 339 mg / CH₂Cl₂ / 1 h / 0 - 20 °C

13.1: 90 percent / H₂ / Rh/Al₂O₃ / tetrahydrofuran / 1 h / 20 °C / 760.05 Torr

14.1: 90 percent / LiBH₄ / methanol; diethyl ether / 3 h / 20 °C

15.1: 91 percent / DMAP; pyridine

16.1: 83 percent / LiN₃; NH₄Cl; DMPU / 16 h / Heating

17.1: 90 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

18.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

19.1: potassium t-butoxide / tetrahydrofuran / 0.02 h / -10 °C

19.2: 77 percent / tetrahydrofuran / 0.08 h

20.1: 72 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; n-butyllithium; jones reagent; calcium hydride; lithium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; silica gel; sodium hydride; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; Rh/Al₂O₃; D-(-)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; Petroleum ether; 2.1: Jones oxidation / 10.1: Sharpless asymmetric epoxidation / 11.1: Dess-Martin oxidation / 12.1: Wittig reaction / 18.1: Swern oxidation;

DOI:10.1021/ol016336a

Reference yield:

(2E,4R,5S,6R)-(+)-methyl-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxy-non-2-enoate ester (364631-50-5) → (4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester (364631-66-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / H₂ / Rh/Al₂O₃ / tetrahydrofuran / 1 h / 20 °C / 760.05 Torr

2.1: 90 percent / LiBH₄ / methanol; diethyl ether / 3 h / 20 °C

3.1: 91 percent / DMAP; pyridine

4.1: 83 percent / LiN₃; NH₄Cl; DMPU / 16 h / Heating

5.1: 90 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

6.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: potassium t-butoxide / tetrahydrofuran / 0.02 h / -10 °C

7.2: 77 percent / tetrahydrofuran / 0.08 h

8.1: 72 percent / aq. HCl / tetrahydrofuran / 3 h / 20 °C

With pyridine; hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; lithium azide; oxalyl dichloride; potassium tert-butylate; hydrogen; ammonium chloride; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 6.1: Swern oxidation;

DOI:10.1021/ol016336a

upstream raw materials:

(4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-benzoate ester

(2E,4R,5S,6R)-(+)-methyl-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxy-non-2-enoate ester

4-benzyloxybutanal

(3R)-6-(benzyloxy)hex-1-yn-3-ol

Downstream raw materials:

(4Z,2S,8S,9S,10R)-(+)-8-azido-13-benzyloxy-10-methoxy-9-[(2R)-3-hydroxy-2-methylpropyl]-2-methyl-9-hydroxytridec-4-en-1-ol

(3R,5S)-(+)-5-[(1'R)-4'-benzyloxy-1'-methoxybutyl]-5-[(4Z,1S,7S)-methyl-1-azido-7-methyloct-4-en-8-oate]-3-methyl-(3H)-furan-2-one