(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

Base Information

Chemical Name:(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one
CAS No.:620949-31-7
Molecular Formula:C₃₉H₅₆O₉Si
Molecular Weight:696.954
Hs Code.:

(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

Synonyms:(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

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Chemical Property of (4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

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Technology Process of (4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

There total 15 articles about (4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one 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: 83.0%

: 620949-22-6
(4aR,5aS,9S,10aR,11aS)-9-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

: 620949-31-7
(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: 620949-31-7
(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 2,6-lutidine / dimethylformamide / 0.5 h / 0 °C

2.1: catecholborane / Rh(PPh₃)3Cl / tetrahydrofuran / 14 h / 20 °C

2.2: 66 percent / aq. H₂O₂; aq. NaHCO₃

3.1: 11 percent / Sc(OTf)3 / benzene / 1.5 h

4.1: NaH; TBAI / tetrahydrofuran; dimethylformamide

5.1: 87 percent / TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 36 h / 20 °C

6.1: Bu₃P / tetrahydrofuran

7.1: aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 40 °C

8.1: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9.1: 81 percent / MeLi / tetrahydrofuran / -78 °C

10.1: (PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / 40 °C

10.2: Dess-Martin periodinane / CH₂Cl₂

11.1: 40 percent / NaBH₄; CoCl₂ / methanol / 15 h / 0 °C

12.1: DBU / toluene / 12 h / Heating

13.1: 83 percent / DDQ / CH₂Cl₂; H₂O

With 2,6-dimethylpyridine; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; methyllithium; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); benzo[1,3,2]dioxaborole; Wilkinson's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

: 620949-05-5
(4aR,6S,7R,8aS)-2,2-Di-tert-butyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

: 620949-31-7
(4aR,5aS,9S,10aR,11aS)-9-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-ylmethyl)-2,2-di-tert-butyl-octahydro-1,3,5,10-tetraoxa-2-sila-cyclohepta[b]naphthalen-8-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: catecholborane / Rh(PPh₃)3Cl / tetrahydrofuran / 14 h / 20 °C

1.2: 66 percent / aq. H₂O₂; aq. NaHCO₃

2.1: 11 percent / Sc(OTf)3 / benzene / 1.5 h

3.1: NaH; TBAI / tetrahydrofuran; dimethylformamide

4.1: 87 percent / TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 36 h / 20 °C

5.1: Bu₃P / tetrahydrofuran

6.1: aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 40 °C

7.1: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

8.1: 81 percent / MeLi / tetrahydrofuran / -78 °C

9.1: (PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / 40 °C

9.2: Dess-Martin periodinane / CH₂Cl₂

10.1: 40 percent / NaBH₄; CoCl₂ / methanol / 15 h / 0 °C

11.1: DBU / toluene / 12 h / Heating

12.1: 83 percent / DDQ / CH₂Cl₂; H₂O

With sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; methyllithium; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); benzo[1,3,2]dioxaborole; Wilkinson's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(03)01862-8