(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

Base Information

• Chemical Name: (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde
• CAS No.: 132375-30-5
• Molecular Formula: C₄₂H₅₆O₆S₂Si
• Molecular Weight: 749.121

Synonyms:(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

Chemical Property of (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

There total 66 articles about (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde 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,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-methanol (132375-84-9) → (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde (132375-30-5)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 1h;

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde (132375-30-5)

Guidance literature:

Multi-step reaction with 35 steps

1: imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

3: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

5: benzene / 17 h / 25 °C

6: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

7: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

8: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

9: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

10: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

11: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

12: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

13: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

14: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

15: benzene / 11 h / 25 °C

16: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

17: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

18: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

19: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

20: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

21: imidazole / CH₂Cl₂ / 1 h / 0 °C

22: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

23: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

24: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

25: TBAF / tetrahydrofuran / 3 h / 25 °C

26: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

27: toluene / 5 h / 25 °C

28: H₂ / Raney-Nickel W₂

29: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

30: imidazole / CH₂Cl₂ / 4 h / 25 °C

31: pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C

32: imidazole / CH₂Cl₂ / 4.5 h / 0 °C

33: TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

34: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 - 0 °C

35: 91 percent / Et₃N, SO₃*py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; Raney-Nickel W₂; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

2,6-Anhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-D-altro-non-8-enitol (122821-83-4) → (2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde (132375-30-5)

Guidance literature:

Multi-step reaction with 33 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

2: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

3: benzene / 17 h / 25 °C

4: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

5: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

6: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

7: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

8: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

9: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

10: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

11: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

12: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

13: benzene / 11 h / 25 °C

14: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

15: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

16: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

17: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

18: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

19: imidazole / CH₂Cl₂ / 1 h / 0 °C

20: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

21: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

22: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

23: TBAF / tetrahydrofuran / 3 h / 25 °C

24: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

25: toluene / 5 h / 25 °C

26: H₂ / Raney-Nickel W₂

27: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

28: imidazole / CH₂Cl₂ / 4 h / 25 °C

29: pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C

30: imidazole / CH₂Cl₂ / 4.5 h / 0 °C

31: TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

32: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 - 0 °C

33: 91 percent / Et₃N, SO₃*py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; Raney-Nickel W₂; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

upstream raw materials:

{(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-methanol

benzyl bromide

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-hydroxymethyl-decahydro-1,8,10-trioxa-anthracen-3-ol

Downstream raw materials:

C₆₅H₉₀O₉S₂Si₂

C₄₇H₇₄O₇S₂Si₂

C₄₇H₇₆O₇S₂Si₂

C₄₉H₈₀O₈Si₃

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