[(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 342901-90-0
• Molecular Formula: C₄₆H₆₄O₇Si
• Molecular Weight: 757.095

Synonyms:[(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

There total 34 articles about [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane 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: 87.0%

[(2S,3R,5R,5aS,6aR,8S,10S,11S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-11-iodomethyl-5a,8-dimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane (669005-93-0) → [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane (342901-90-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

benzyl bromide (100-39-0) → [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane (342901-90-0)

Guidance literature:

Multi-step reaction with 27 steps

1.1: n-Bu₂SnO / benzene / Heating

1.2: CsF / dimethylformamide / 20 °C

2.1: NaH; CS₂; MeI / tetrahydrofuran / 20 °C

2.2: n-Bu₃SnH; AIBN / benzene / Heating

3.1: conc. HCl / CHCl₃ / 20 °C

3.2: 46 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

5.1: 98 percent / MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

6.1: SmI₂; HMPA / methanol; tetrahydrofuran / 0 °C

7.1: LiAlH₄ / tetrahydrofuran / 20 °C

8.1: 84 percent / NaH / dimethylformamide / 20 °C

9.1: 89 percent / camphorsulfonic acid / methanol / 20 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

11.1: camphorsulfonic acid / methanol / 0 °C

12.1: I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

13.1: t-BuOK / tetrahydrofuran / 20 °C

14.1: 9-BBN / tetrahydrofuran / 20 °C

14.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

15.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

15.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

16.1: 80 percent / t-BuOK; n-Bu₄NI / tetrahydrofuran / 20 °C

17.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

18.1: 100 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

19.1: DDQ / CH₂Cl₂; H₂O; various solvent(s) / 20 °C

20.1: Zn(OTf)2 / CH₂Cl₂ / 20 °C

21.1: DMAP; Et₃N / CH₂Cl₂ / 0 °C

22.1: 96 percent / mCPBA / CH₂Cl₂ / 20 °C

23.1: CH₂Cl₂ / -78 - 0 °C

23.2: 83 percent / K₂CO₃ / methanol / 20 °C

24.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

25.1: camphorsulfonic acid / methanol; CH₂Cl₂ / 0 °C

26.1: 94 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

27.1: 87 percent / t-BuOK / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 14.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) → [(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane (342901-90-0)

Guidance literature:

Multi-step reaction with 26 steps

1.1: NaH; CS₂; MeI / tetrahydrofuran / 20 °C

1.2: n-Bu₃SnH; AIBN / benzene / Heating

2.1: conc. HCl / CHCl₃ / 20 °C

2.2: 46 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

3.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

4.1: 98 percent / MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

5.1: SmI₂; HMPA / methanol; tetrahydrofuran / 0 °C

6.1: LiAlH₄ / tetrahydrofuran / 20 °C

7.1: 84 percent / NaH / dimethylformamide / 20 °C

8.1: 89 percent / camphorsulfonic acid / methanol / 20 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

10.1: camphorsulfonic acid / methanol / 0 °C

11.1: I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

12.1: t-BuOK / tetrahydrofuran / 20 °C

13.1: 9-BBN / tetrahydrofuran / 20 °C

13.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

14.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

14.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

15.1: 80 percent / t-BuOK; n-Bu₄NI / tetrahydrofuran / 20 °C

16.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

17.1: 100 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

18.1: DDQ / CH₂Cl₂; H₂O; various solvent(s) / 20 °C

19.1: Zn(OTf)2 / CH₂Cl₂ / 20 °C

20.1: DMAP; Et₃N / CH₂Cl₂ / 0 °C

21.1: 96 percent / mCPBA / CH₂Cl₂ / 20 °C

22.1: CH₂Cl₂ / -78 - 0 °C

22.2: 83 percent / K₂CO₃ / methanol / 20 °C

23.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

24.1: camphorsulfonic acid / methanol; CH₂Cl₂ / 0 °C

25.1: 94 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

26.1: 87 percent / t-BuOK / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; 13.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

upstream raw materials:

[(2S,3R,5R,5aS,6aR,8S,10S,11S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-11-iodomethyl-5a,8-dimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

benzyl bromide

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Downstream raw materials:

C₇₅H₁₀₀O₁₂Si

C₇₁H₉₀O₁₂S

C₇₅H₁₀₂O₁₃Si

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