(2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Base Information

• Chemical Name: (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran
• CAS No.: 131310-76-4
• Molecular Formula: C₅₀H₈₀O₇Si₃
• Molecular Weight: 877.437

Synonyms:

Chemical Property of (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

There total 25 articles about (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran 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: 92.0%

(2R,3S,4aR,6S,7R,8aS)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-2-hydroxymethyl-7-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol (131310-75-3,131351-12-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran (131310-76-4,131432-68-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran (131310-76-4,131432-68-3)

Guidance literature:

Multi-step reaction with 25 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

4: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

5: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

6: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

7: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

9: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 0 °C

10: 97 percent / imidazole / dimethylformamide / 10.5 h / 50 °C

11: 1.) 9-BBN, 2.) NaOH, hydrogen peroxide / 1.) THF, 25 deg C, 40 min, 2.) 30 min.

12: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

13: 88 percent / benzoic acid / benzene / 0.5 h / 50 °C

14: 98 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

15: 1.) (-)-diethyl tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -28 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

16: 93 percent / triethylamine, sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 3 h / 0 °C

17: 88 percent / benzoic acid / benzene / 0.5 h / 25 °C

18: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

19: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 13 h / 25 °C

20: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 48 h

21: 95 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

22: 89 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

23: 1.) KH / 1.) THF, mineral oil, 50 deg C, 40 min, 2.) 10 min

24: 86 percent / Camphorsulfonic acid / methanol / 1 h / 0 °C

25: 92 percent / imidazole / dimethylformamide / 12 h / 50 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; palladium on activated charcoal; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

(E)-(5S,6R)-5,6,7-Trihydroxy-2-methyl-hept-2-enoic acid ethyl ester (131310-54-8) → (2S,3R,4aS,6R,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran (131310-76-4,131432-68-3)

Guidance literature:

Multi-step reaction with 24 steps

1: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

2: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

3: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

4: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

5: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

6: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

7: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

8: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 0 °C

9: 97 percent / imidazole / dimethylformamide / 10.5 h / 50 °C

10: 1.) 9-BBN, 2.) NaOH, hydrogen peroxide / 1.) THF, 25 deg C, 40 min, 2.) 30 min.

11: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

12: 88 percent / benzoic acid / benzene / 0.5 h / 50 °C

13: 98 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

14: 1.) (-)-diethyl tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -28 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

15: 93 percent / triethylamine, sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 3 h / 0 °C

16: 88 percent / benzoic acid / benzene / 0.5 h / 25 °C

17: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

18: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 13 h / 25 °C

19: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 48 h

20: 95 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

21: 89 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

22: 1.) KH / 1.) THF, mineral oil, 50 deg C, 40 min, 2.) 10 min

23: 86 percent / Camphorsulfonic acid / methanol / 1 h / 0 °C

24: 92 percent / imidazole / dimethylformamide / 12 h / 50 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; palladium on activated charcoal; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)85579-4

upstream raw materials:

(2R,3S,4aR,6S,7R,8aS)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-2-hydroxymethyl-7-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

tert-butyldimethylsilyl chloride

2-deoxy-D-ribose

(E)-(5S,6R)-5,6,7-Trihydroxy-2-methyl-hept-2-enoic acid ethyl ester

Downstream raw materials:

[(2R,3S,4aR,6S,7R,8aS)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-7-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(4-Methoxy-benzyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-2-methyl-propan-1-ol

4,8:7,11:10,14-Trianhydro-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-2,12-dimethyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enoic acid

3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(4-Methoxy-benzyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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