(4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Base Information

• Chemical Name: (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane
• CAS No.: 911837-54-2
• Molecular Formula: C₅₆H₈₆O₈Si₃
• Molecular Weight: 971.551
• Mol file: 911837-54-2.mol

Synonyms:(4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Chemical Property of (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

There total 15 articles about (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane 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: 95.0%

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,6-dimethyl-nonane-1,3-diol (911837-44-0) + p-Anisaldehyde dimethyl acetal (2186-92-7) → (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane (911837-54-2)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2006.06.173

Reference yield:

(-)-(R)-4-benzyl-3-[(2R,3S)-5-(benzyloxy)-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one (870091-89-7) → (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane (911837-54-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 95 percent / imidazole / dimethylformamide

2: 90 percent / NaBH₄ / tetrahydrofuran; H₂O

3: 96 percent / Bu₂BOTf; Et₃N

4: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

5: 95 percent / CSA / CH₂Cl₂

6: 95 percent / DIBAL-H / CH₂Cl₂ / 0 °C

7: 95 percent / 4-DMAP; pyridine / CH₂Cl₂; dimethylformamide

8: 90 percent / OsO₄; NMO; NaIO₄ / 2-methyl-propan-2-ol; H₂O

9: 100 percent / NaBH₄ / methanol

10: 95 percent / imidazole / dimethylformamide

11: 90 percent / H₂ / Raney Nickel / ethanol

12: 92 percent / TEMPO; IBDA

13: 90 percent / Bu₂BOTf; DIPEA

14: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

15: 95 percent / CSA / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Swern oxidation / 4: Evans aldol condensation / 14: Evans aldol condensation;

DOI:10.1016/j.tetlet.2006.06.173

Reference yield:

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol (872369-16-9) → (4S,5S)-4-[(2S,3S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-hexyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane (911837-54-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 96 percent / Bu₂BOTf; Et₃N

2: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

3: 95 percent / CSA / CH₂Cl₂

4: 95 percent / DIBAL-H / CH₂Cl₂ / 0 °C

5: 95 percent / 4-DMAP; pyridine / CH₂Cl₂; dimethylformamide

6: 90 percent / OsO₄; NMO; NaIO₄ / 2-methyl-propan-2-ol; H₂O

7: 100 percent / NaBH₄ / methanol

8: 95 percent / imidazole / dimethylformamide

9: 90 percent / H₂ / Raney Nickel / ethanol

10: 92 percent / TEMPO; IBDA

11: 90 percent / Bu₂BOTf; DIPEA

12: 93 percent / NaBH₄ / tetrahydrofuran; H₂O

13: 95 percent / CSA / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Swern oxidation / 2: Evans aldol condensation / 12: Evans aldol condensation;

DOI:10.1016/j.tetlet.2006.06.173

upstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,6-dimethyl-nonane-1,3-diol

p-Anisaldehyde dimethyl acetal

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

(?)-(2S,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-ol

Downstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-3,7-bis-(4-methoxy-benzyloxy)-2,6-dimethyl-nonanal

5-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-9-(tert-butyl-diphenyl-silanyloxy)-3,7-bis-(4-methoxy-benzyloxy)-2,6-dimethyl-nonan-1-ol

Refernces