[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 436153-75-2
• Molecular Formula: C₃₇H₅₆O₆Si
• Molecular Weight: 624.934

Synonyms:[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane

There total 54 articles about [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-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: 94.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol (436153-91-2) → [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane (436153-75-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ol025814u

Reference yield:

(5R,6S)-5,9-Bis-benzyloxy-6-methoxymethoxy-6-methyl-nonanal → [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane (436153-75-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

2.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

3.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

4.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

5.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

6.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

7.1: 51 percent / DBU / toluene / 12 h / 110 °C

8.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

9.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

10.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

11.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

12.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

13.1: AIBN; n-Bu₃SnH / toluene / 0.83 h / 100 °C

14.1: 0.931 g / DDQ / CH₂Cl₂; aq. phosphate buffer / 2.5 h / 20 °C / pH 7

15.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja042686r

Reference yield:

(4S,5R)-5-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-4-methyl-nonanal → [(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy]-tert-butyl-dimethyl-silane (436153-75-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 5.67 g / NaBH₄ / methanol / 0.5 h / 0 °C

2.1: potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

3.1: 5.23 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

4.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / 0 °C

5.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

6.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

7.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

8.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

8.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

9.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

10.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

11.1: 51 percent / DBU / toluene / 12 h / 110 °C

12.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

13.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

14.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

15.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

16.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

17.1: AIBN; n-Bu₃SnH / toluene / 0.83 h / 100 °C

18.1: 0.931 g / DDQ / CH₂Cl₂; aq. phosphate buffer / 2.5 h / 20 °C / pH 7

19.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.1: Swern oxidation / 8.2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja042686r

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2,9-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

(4R,5S)-1-[1,3]Dioxan-2-yl-5-methoxymethoxy-5,9-dimethyl-dec-8-en-4-ol

Triethyl-((2R,4aR,7R,8aS)-6-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

Downstream raw materials:

Phosphoric acid (4aS,5aR,6aS,8R,9S,10aR,11aS,13aR)-9-(tert-butyl-dimethyl-silanyloxy)-4a,8-dimethyl-4a,5a,6,6a,8,9,10,10a,11a,12,13,13a-dodecahydro-4H-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-2-yl ester diphenyl ester

C₆₂H₈₈O₁₂Si

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