(1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol

Base Information

• Chemical Name: (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol
• CAS No.: 103795-27-3
• Molecular Formula: C₄₈H₅₁NO₇S
• Molecular Weight: 786.001

Synonyms:

Chemical Property of (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol

There total 24 articles about (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol 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:

benzyl bromide (100-39-0) → (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol (103795-27-3)

Guidance literature:

Multi-step reaction with 22 steps

1: 1.) 50percent NaH, 2.) tetra-n-butylammonium iodide / 1.) reflux, 20 min, 2.) room temp., overnight

2: 94 percent / acetonitrile / 7 h / Heating

3: 70 percent / NaBH₄ / methanol / 0.5 h / -10 °C

4: 86 percent / H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

5: CH₂Cl₂ / 12 h / Ambient temperature

6: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

7: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

8: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

9: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

10: CH₂Cl₂ / 12 h / Ambient temperature

11: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

12: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

13: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

14: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

15: CH₂Cl₂ / 12 h / Ambient temperature

16: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

17: 1.) NaBH₄, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

18: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

19: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

20: CH₂Cl₂ / 12 h / Ambient temperature

21: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

22: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00264a035

Reference yield:

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6) → (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol (103795-27-3)

Guidance literature:

Multi-step reaction with 18 steps

1: CH₂Cl₂ / 12 h / Ambient temperature

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

3: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

4: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

5: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

6: CH₂Cl₂ / 12 h / Ambient temperature

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

8: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

9: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

10: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

11: CH₂Cl₂ / 12 h / Ambient temperature

12: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

13: 1.) NaBH₄, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

14: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

15: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

16: CH₂Cl₂ / 12 h / Ambient temperature

17: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

18: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo00264a035

Reference yield:

2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-thiazole (103795-09-1) → (1R)-1,2,3,4,5-penta-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol (103795-27-3)

Guidance literature:

Multi-step reaction with 23 steps

1: 1 M tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

2: 1.) 50percent NaH, 2.) tetra-n-butylammonium iodide / 1.) reflux, 20 min, 2.) room temp., overnight

3: 94 percent / acetonitrile / 7 h / Heating

4: 70 percent / NaBH₄ / methanol / 0.5 h / -10 °C

5: 86 percent / H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

6: CH₂Cl₂ / 12 h / Ambient temperature

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

8: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

9: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

10: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

11: CH₂Cl₂ / 12 h / Ambient temperature

12: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

13: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

14: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

15: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

16: CH₂Cl₂ / 12 h / Ambient temperature

17: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

18: 1.) NaBH₄, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

19: 2.) NaBH₄ / 1.) CH₃CN, reflux, 2.) CH₃OH, -10 deg C, 30 min

20: H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

21: CH₂Cl₂ / 12 h / Ambient temperature

22: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

23: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00264a035

upstream raw materials:

benzyl bromide

(1R)-2,3,4,5-tetra-O-benzyl-6,7-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-glycero-heptitol

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-thiazole

Downstream raw materials:

2,3,4,5,6-penta-O-benzyl-7,8-O-isopropylidene-D-allo-D-erythro-octose

2-[(1R,2R,3R,4R,5R,6R)-2,3,4,5,6-Pentakis-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-trimethylsilanyloxy-hexyl]-thiazole

(1S,2S,3S,4S,5R,6R)-2,3,4,5,6-Pentakis-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-hexan-1-ol

(1R)-2,3,4,5,6-penta-O-benzyl-7,8-O-isopropylidene-1-(2-thiazolyl)-D-allo-D-erythro-octitol

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