(4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester

Base Information

• Chemical Name: (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester
• CAS No.: 364631-52-7
• Molecular Formula: C₃₀H₅₁N₃O₈
• Molecular Weight: 581.75
• Mol file: 364631-52-7.mol

Synonyms:(4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester

Chemical Property of (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester

There total 17 articles about (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate 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: 83.0%

2,2-Dimethyl-propionic acid 3-{(2R,3S)-3-((R)-4-benzyloxy-1-methoxy-butyl)-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-oxiranyl}-propyl ester (364631-51-6) → (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester (364631-52-7)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium azide; ammonium chloride; for 16h; Heating;

DOI:10.1021/ol016336a

Reference yield:

4-benzyloxybutanal (5470-84-8) → (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester (364631-52-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 80 percent / tetrahydrofuran / 0 °C

2: 85 percent / Jones reagent / 0 °C

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

4: 80 percent / imidazole / CH₂Cl₂ / 20 °C

5: 90 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 70 percent / CuBr*DMS / tetrahydrofuran / -78 - 20 °C

7: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

8: 76 percent / NaH / dimethylformamide; various solvent(s) / 5 h / 0 - 20 °C

9: 91 percent / diisobutylaluminium hydride / CH₂Cl₂; petroleum ether / 2 h / -78 °C

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

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

12: 339 mg / CH₂Cl₂ / 1 h / 0 - 20 °C

13: 90 percent / H₂ / Rh/Al₂O₃ / tetrahydrofuran / 1 h / 20 °C / 760.05 Torr

14: 90 percent / LiBH₄ / methanol; diethyl ether / 3 h / 20 °C

15: 91 percent / DMAP; pyridine

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

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium borohydride; n-butyllithium; jones reagent; calcium hydride; lithium azide; copper(I) bromide dimethylsulfide complex; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; tetrabutyl ammonium fluoride; hydrogen; silica gel; sodium hydride; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; titanium(IV) isopropylate; Rh/Al₂O₃; D-(-)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; Petroleum ether; 2: Jones oxidation / 10: Sharpless asymmetric epoxidation / 11: Dess-Martin oxidation / 12: Wittig reaction;

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) → (4S,5S,6R)-(+)-tert-butyl-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononanoate ester (364631-52-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 90 percent / LiBH₄ / methanol; diethyl ether / 3 h / 20 °C

3: 91 percent / DMAP; pyridine

4: 83 percent / LiN₃; NH₄Cl; DMPU / 16 h / Heating

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium borohydride; lithium azide; hydrogen; ammonium chloride; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/ol016336a

upstream raw materials:

2,2-Dimethyl-propionic acid 3-{(2R,3S)-3-((R)-4-benzyloxy-1-methoxy-butyl)-3-[(R)-3-(2-methoxy-ethoxymethoxy)-2-methyl-propyl]-oxiranyl}-propyl 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

pivaloyl chloride

Downstream 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

(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

(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