(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

Base Information

Chemical Name:(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one
CAS No.:470470-76-9
Molecular Formula:C₄₅H₇₄O₈Si₂
Molecular Weight:799.249
Hs Code.:

Synonyms:(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

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Chemical Property of (3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

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Technology Process of (3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

There total 21 articles about (3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-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: 69.0%

: 470470-74-7
(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane

: 470470-76-9
(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

Guidance literature:: (3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane; With osmium(VIII) oxide; sodium carbonate; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 18h;

With sodium periodate; sodium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2011.09.064

Reference yield: 69.0%

: 470470-75-8
(2S,6R)-2-{(2S,4S,6S)-4-Benzyloxy-6-[(S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-butyl]-2-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl}-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-tetrahydro-pyran-4-ol

: 470470-76-9
(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

Guidance literature:: With sodium periodate; sodium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 470470-76-9
(3S,5S,7S,9S,11S,15R)-1,7-dibenzyloxy-3,16-bis-(tert-butyldimethylsilyloxy)-5,9-epoxy-11,15-epoxy-9-methoxy-8,8-dimethylhexadecan-13-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: 97 percent / imid.; DMAP; TBAI / 0.5 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

2.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 49 percent / LDA / 0.03 h / -78 °C

5.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

6.1: 74 percent / PPTS / 18 h / 20 °C

7.1: 95 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

8.1: 100 percent / (COCl)2; DMSO; Et₃N / -78 °C

9.1: 100 percent / tetrahydrofuran / -78 - 20 °C

10.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

11.1: 55 percent / ZnI₂; 4 Angstroem MS / CH₂Cl₂ / 18 h / 20 °C / protect from light

12.1: HF / H₂O; acetonitrile / 24 h / 20 °C

12.2: 34 percent / PPTS / methanol / 3 h / 20 °C

13.1: 100 percent / imid.; TBAI; DMAP / CH₂Cl₂ / 20 °C

14.1: 55 percent / Na₂CO₃; OsO₄; NMO / acetone; butan-1-ol; H₂O / 18 h / 20 °C

15.1: 69 percent / NaIO₄; Na₂CO₃ / methanol; tetrahydrofuran; H₂O / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 4 Angstroem MS; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; zinc(II) iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetone; acetonitrile; butan-1-ol;
DOI:10.1016/S0040-4039(02)01054-7