(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

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Chemical Name:(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol
CAS No.:364631-64-1
Molecular Formula:C₂₅H₄₃N₃O₇
Molecular Weight:497.632
Hs Code.:

Synonyms:(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

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Chemical Property of (4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

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Technology Process of (4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

There total 17 articles about (4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol 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: 90.0%

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

: 364631-64-1
(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 24h;
DOI:10.1021/ol016336a

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 364631-64-1
(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

Guidance literature:: Multi-step reaction with 17 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

17: 90 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

With pyridine; 1H-imidazole; 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; 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; water; 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:

: 364631-50-5
(2E,4R,5S,6R)-(+)-methyl-9-benzyloxy-6-methoxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4,5-epoxy-non-2-enoate ester

: 364631-64-1
(4S,5S,6R)-(-)-9-benzyloxy-6-methoxy-5-hydroxy-5-[(2R)-3-methoxyethoxymethoxy-2-methylpropyl]-4-azidononan-1-ol

Guidance literature:: Multi-step reaction with 5 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

5: 90 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; lithium azide; hydrogen; ammonium chloride; Rh/Al₂O₃; In tetrahydrofuran; methanol; diethyl ether; water;
DOI:10.1021/ol016336a