(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Base Information

Chemical Name:(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole
CAS No.:214261-07-1
Molecular Formula:C₄₃H₅₄INO₃
Molecular Weight:759.811
Hs Code.:

(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Synonyms:(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

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Chemical Property of (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

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Technology Process of (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

There total 14 articles about (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole 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: 100.0%

: 76-83-5
trityl chloride

: 214261-05-9
(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole-3-methanol

: 214261-07-1
(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Guidance literature:: In pyridine; at 70 ℃;
DOI:10.1021/jo980813u

Reference yield:

: 214260-97-6
(S)-3-methylhex-5-yn-1-ol

: 214261-07-1
(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) Cp₂ZrCl₂, 2.) I₂ / 1.) ClH₂CH₂Cl, rt, 24 h, 2.) ClCH₂CH₂Cl, THF_. -20 deg C, 2 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 - -60 deg C, 30 in, 2.) CH₂Cl₂, -60 deg C to rt

3: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

4: NH₂OH*HCl, KOH / dimethylformamide; ethyl acetate / 3 h / 100 °C

5: 0.547 g / aq. HCl / tetrahydrofuran / 3 h / Heating

6: 99 percent / toluene / 4 h / 80 °C

7: 1.) CaCO₃, 4 Angstroem MS / 1.) PhMe, 40 deg C, 4 h, 2.) PhMe, 80 deg C, 18 h

8: 89 percent / DIBALH / toluene / 2 h / -78 °C

9: 100 percent / pyridine / 70 °C

With hydrogenchloride; potassium hydroxide; n-butyllithium; zirconocene dichloride; oxalyl dichloride; 4 Angstroem MS; hydroxylamine hydrochloride; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; calcium carbonate; In tetrahydrofuran; pyridine; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo980813u

Reference yield:

: 214260-96-5
(4R,2''RS)-4-methyl-6-(2-tetrahydropyranyloxy)1-hexyne

: 214261-07-1
(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole

Guidance literature:: Multi-step reaction with 10 steps

1: CSA / methanol / 1 h / Ambient temperature

2: 1.) Cp₂ZrCl₂, 2.) I₂ / 1.) ClH₂CH₂Cl, rt, 24 h, 2.) ClCH₂CH₂Cl, THF_. -20 deg C, 2 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 - -60 deg C, 30 in, 2.) CH₂Cl₂, -60 deg C to rt

4: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

5: NH₂OH*HCl, KOH / dimethylformamide; ethyl acetate / 3 h / 100 °C

6: 0.547 g / aq. HCl / tetrahydrofuran / 3 h / Heating

7: 99 percent / toluene / 4 h / 80 °C

8: 1.) CaCO₃, 4 Angstroem MS / 1.) PhMe, 40 deg C, 4 h, 2.) PhMe, 80 deg C, 18 h

9: 89 percent / DIBALH / toluene / 2 h / -78 °C

10: 100 percent / pyridine / 70 °C

With hydrogenchloride; potassium hydroxide; n-butyllithium; zirconocene dichloride; oxalyl dichloride; 4 Angstroem MS; camphor-10-sulfonic acid; hydroxylamine hydrochloride; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; calcium carbonate; In tetrahydrofuran; pyridine; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo980813u