4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione

Base Information

• Chemical Name: 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione
• CAS No.: 108926-38-1
• Molecular Formula: C₃₇H₅₅NO₇Si₂
• Molecular Weight: 682.017
• Mol file: 108926-38-1.mol

Synonyms:

Chemical Property of 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione

There total 21 articles about 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione 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%

(4'S,5'R,6'R)-4-6'-1,4-dihydroxy-2-methyl-3-methylene-butyryl-5'-tert-butyldimethylsiloxy-1'-3'-dioxan-4'-yl-2,6-piperidinedione (108926-37-0,120786-85-8,120786-88-1,120786-89-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione (108926-38-1,120786-86-9,120786-87-0,120787-73-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86175-5

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione (108926-38-1,120786-86-9,120786-87-0,120787-73-7)

Guidance literature:

Multi-step reaction with 18 steps

1: 73 percent / 12 M HCl, AcOH / 0.08 h / Ambient temperature

2: 92 percent / toluene / 0.01 h / Heating

3: 79 percent / TMSOTf, 2,6-Lu / 0.25 h / 0 °C / further reag.

4: 1.) 50 percent NaH oil dispersion; 2.) n-Bu₄NBr / 1.) THF, reflux, 15 min; 2.) THF, RT, 12 h

5: NaCl, H₂O / dimethylsulfoxide / 1 h / 160 °C

6: 1 M KOH / methanol / 48 h / Ambient temperature

7: MeOCOCl, Et₃N / tetrahydrofuran / 3 h / -20 °C

8: NH₃ / 0.5 h / 0 °C

9: Ac₂O / 0.33 h / 100 °C / sodium acetate buffer

10: 95 percent / H₂ / 10 percent Pd-C / acetic acid; methanol / 2 h / Ambient temperature

11: 91 percent / Py / 2.5 h / 0 °C

12: 86 percent / 2.6-Lu / CH₂Cl₂ / 0.17 h / Ambient temperature

13: 87 percent / i-Bu₂AlH / CH₂Cl₂ / 1 h / -78 °C

14: 84 percent / CrO₃*2Py / CH₂Cl₂ / 0.25 h / Ambient temperature

15: 73 percent / Zn / tetrahydrofuran / 0.1 h / Heating

16: i-Bu₂AlH / hexane; CH₂Cl₂ / 1 h / -78 °C

17: NaBH₄, CeCl₃*7H₂O / 0.17 h / 0 °C

18: 90 percent / imidazole / dimethylformamide / 0.67 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; ammonia; water; hydrogen; acetic anhydride; dipyridine chromium trioxide; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; methyl chloroformate; sodium chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86175-5

Reference yield:

3,5-di-O-benzyl-D-xylofuranose (16054-77-6,120693-82-5,120693-83-6) → 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione (108926-38-1,120786-86-9,120786-87-0,120787-73-7)

Guidance literature:

Multi-step reaction with 17 steps

1: 92 percent / toluene / 0.01 h / Heating

2: 79 percent / TMSOTf, 2,6-Lu / 0.25 h / 0 °C / further reag.

3: 1.) 50 percent NaH oil dispersion; 2.) n-Bu₄NBr / 1.) THF, reflux, 15 min; 2.) THF, RT, 12 h

4: NaCl, H₂O / dimethylsulfoxide / 1 h / 160 °C

5: 1 M KOH / methanol / 48 h / Ambient temperature

6: MeOCOCl, Et₃N / tetrahydrofuran / 3 h / -20 °C

7: NH₃ / 0.5 h / 0 °C

8: Ac₂O / 0.33 h / 100 °C / sodium acetate buffer

9: 95 percent / H₂ / 10 percent Pd-C / acetic acid; methanol / 2 h / Ambient temperature

10: 91 percent / Py / 2.5 h / 0 °C

11: 86 percent / 2.6-Lu / CH₂Cl₂ / 0.17 h / Ambient temperature

12: 87 percent / i-Bu₂AlH / CH₂Cl₂ / 1 h / -78 °C

13: 84 percent / CrO₃*2Py / CH₂Cl₂ / 0.25 h / Ambient temperature

14: 73 percent / Zn / tetrahydrofuran / 0.1 h / Heating

15: i-Bu₂AlH / hexane; CH₂Cl₂ / 1 h / -78 °C

16: NaBH₄, CeCl₃*7H₂O / 0.17 h / 0 °C

17: 90 percent / imidazole / dimethylformamide / 0.67 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; ammonia; water; hydrogen; acetic anhydride; dipyridine chromium trioxide; sodium hydride; diisobutylaluminium hydride; triethylamine; methyl chloroformate; sodium chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86175-5

upstream raw materials:

(4'S,5'R,6'R)-4-6'-1,4-dihydroxy-2-methyl-3-methylene-butyryl-5'-tert-butyldimethylsiloxy-1'-3'-dioxan-4'-yl-2,6-piperidinedione

tert-butylchlorodiphenylsilane

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

(-)-sesbanimide B

(+)-sesbanimide A

Refernces