(1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

Base Information

Chemical Name:(1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol
CAS No.:103795-23-9
Molecular Formula:C₄₀H₄₃NO₆S
Molecular Weight:665.851
Hs Code.:

Synonyms:

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Chemical Property of (1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

Chemical Property:

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Technology Process of (1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

There total 19 articles about (1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol 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:

: 100-39-0
benzyl bromide

: 103795-23-9
(1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

Guidance literature:: Multi-step reaction with 17 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

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:

: 103795-12-6
(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

: 103795-23-9
(1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

Guidance literature:: Multi-step reaction with 13 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

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:

: 103795-09-1
2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-thiazole

: 103795-23-9
(1R)-1,2,3,4-tetra-O-benzyl-5,6-O-isopropylidene-1-(2-thiazolyl)-D-allitol

Guidance literature:: Multi-step reaction with 18 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

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