9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Base Information

Chemical Name:9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol
CAS No.:871912-73-1
Molecular Formula:C₇₃H₉₀O₉Si
Molecular Weight:1139.6
Hs Code.:

9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(<i>tert</i>-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Synonyms:9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Chemical Property of 9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Technology Process of 9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

There total 12 articles about 9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-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: 87.0%

: 871912-72-0
(2R,3S,4S,4aR,6S,8R,9S,9aS)-9-Benzyloxy-6-[(2R,3S,5R,7R,8S)-7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-(3-hydroxy-propyl)-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 871912-73-1
9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4aR,6S,7R,9S,10aS)-6-Hydroxymethyl-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

: 871912-73-1
9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: tBuOK; TBAI / tetrahydrofuran / 0.5 h / 23 °C

2.1: ethanedithiol; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

3.1: 93 percent / PPTS / benzene / 12 h / Heating

4.1: 85 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 2 h / 23 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

6.1: NHMDS / tetrahydrofuran / 0.25 h / -20 °C

7.1: LDA / tetrahydrofuran / 0.25 h / -20 °C

7.2: 98 percent / tetrahydrofuran / 0.5 h / -78 °C

8.1: 69 percent / PTS / methanol / 0.5 h / 23 °C

9.1: 73 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 87 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; ethandithiol; lithium aluminium tetrahydride; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-6-benzyloxymethyl-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocyclooctene

: 871912-73-1
9-benzyloxy-6-[7-benzyloxy-8-benzyloxymethyl-5-methyl-3-(naphthalen-2-ylmethoxy)-oxocan-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,4,8-trimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: ethanedithiol; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

2.1: 93 percent / PPTS / benzene / 12 h / Heating

3.1: 85 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 2 h / 23 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

5.1: NHMDS / tetrahydrofuran / 0.25 h / -20 °C

6.1: LDA / tetrahydrofuran / 0.25 h / -20 °C

6.2: 98 percent / tetrahydrofuran / 0.5 h / -78 °C

7.1: 69 percent / PTS / methanol / 0.5 h / 23 °C

8.1: 73 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 87 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; ethandithiol; lithium aluminium tetrahydride; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetlet.2005.09.164