(1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-1-ol

Base Information

• Chemical Name: (1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-1-ol
• CAS No.: 118377-24-5
• Molecular Formula: C₃₉H₄₅NO₉S
• Molecular Weight: 703.854

Synonyms:

Chemical Property of (1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-1-ol

There total 34 articles about (1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-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:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → (9S)-6,7,8-tri-O-benzyl-1,2:3,4-di-O-isopropylidene-9-(2-thiazolyl)-α-D-galacto-D-ribo-nonulo-1,5-pyranose (118377-24-5)

Guidance literature:

Multi-step reaction with 17 steps

1: CH₂Cl₂ / 12 h / 0 °C

2: 1 M 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: 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: 12 h / Ambient temperature

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

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:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → (1R,2R,3R,4R)-2,3,4-Tris-benzyloxy-4-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-butan-1-ol (118377-24-5)

Guidance literature:

Multi-step reaction with 17 steps

1: CH₂Cl₂ / 12 h / 0 °C

2: 1 M 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: 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: 12 h / Ambient temperature

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

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:

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-D-glycero-heptodialdo-1,5-pyranose (91861-00-6) → (9S)-6,7,8-tri-O-benzyl-1,2:3,4-di-O-isopropylidene-9-(2-thiazolyl)-α-D-galacto-D-ribo-nonulo-1,5-pyranose (118377-24-5)

Guidance literature:

Multi-step reaction with 12 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: 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: 12 h / Ambient temperature

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

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

DOI:10.1021/jo00264a035

upstream raw materials:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-D-glycero-heptodialdo-1,5-pyranose

(6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

6,7-di-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-D-erythro-octodialdo-1,5-pyranose

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