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

Base Information

• Chemical Name: (2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-ol
• CAS No.: 132375-80-5
• Molecular Formula: C₄₄H₆₄O₇Si₂
• Molecular Weight: 761.159

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 62 articles about (2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-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: 93.0%

(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 (132375-81-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (132375-80-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; 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,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (132375-80-5)

Guidance literature:

Multi-step reaction with 32 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

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; 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-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-82-3) → (2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-ol (132375-80-5)

Guidance literature:

Multi-step reaction with 31 steps

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

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

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

4: benzene / 17 h / 25 °C

5: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

6: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

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

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

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

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

11: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

12: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

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

14: benzene / 11 h / 25 °C

15: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

16: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

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

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

19: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

20: imidazole / CH₂Cl₂ / 1 h / 0 °C

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

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

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

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

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

26: toluene / 5 h / 25 °C

27: H₂ / Raney-Nickel W₂

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

29: imidazole / CH₂Cl₂ / 4 h / 25 °C

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

31: imidazole / CH₂Cl₂ / 4.5 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; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; 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

upstream raw materials:

(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

tert-butyldimethylsilyl chloride

tert-butylchlorodiphenylsilane

benzyl bromide

Downstream raw materials:

(Z)-(4aR,6S,7R,10aS)-6-{(Z)-3-[(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-3,3-bis-ethylsulfanyl-7-(3-hydroxy-propyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-allyl}-2-phenyl-4,4a,6,7,10,10a-hexahydro-1,3,5-trioxa-benzocycloocten-7-ol

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

C₄₉H₆₄O₉Si

C₅₄H₇₂O₁₀Si

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