(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

Base Information

Chemical Name:(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol
CAS No.:182001-29-2
Molecular Formula:C₂₃H₃₄INO₂
Molecular Weight:483.433
Hs Code.:

Synonyms:(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

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Chemical Property of (7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

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Technology Process of (7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

There total 15 articles about (7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-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: 88.0%

: 182001-21-4
(3R,4R,4aS)-4-Benzyloxy-4-methyl-3-((R)-3-methyl-hept-1-ynyl)-hexahydro-pyrrolo[1,2-c][1,3]oxazine

: 182001-29-2
(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

Guidance literature:: With formaldehyd; camphor-10-sulfonic acid; sodium iodide; at 100 ℃; for 1h;
DOI:10.1021/ja961640y

Reference yield:

: 123190-86-3
(1R,7aS)-tetrahydro-1-methyl-1-(hydroxymethyl)-1H,3H-pyrrolo<1,2-c>oxazol-3-one

: 182001-29-2
(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 14 h / Ambient temperature

2: aq. KOH / ethanol / 16 h / 80 °C

3: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

5: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

6: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, a) -78 deg C, 2 h, b) -50 deg C, 8 h

8: 90 percent / AgNO₃ / ethanol / 20 h / Ambient temperature

9: 88 percent / NaI, aq. CH₂O, camphorsulfonic acid monohydrate / 1 h / 100 °C

With potassium hydroxide; lithium tetrafluoroborate; n-butyllithium; formaldehyd; oxalyl dichloride; camphor-10-sulfonic acid; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y

Reference yield:

: 66050-98-4
(2R)-methyl-1-hexanol

: 182001-29-2
(7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

2: 1.) Ph₃P / 1.) CH₂Cl₂, -10 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 10 min, b) -20 deg C, 30 min

3: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, a) -78 deg C, 2 h, b) -50 deg C, 8 h

4: 90 percent / AgNO₃ / ethanol / 20 h / Ambient temperature

5: 88 percent / NaI, aq. CH₂O, camphorsulfonic acid monohydrate / 1 h / 100 °C

With n-butyllithium; formaldehyd; oxalyl dichloride; camphor-10-sulfonic acid; silver nitrate; dimethyl sulfoxide; triphenylphosphine; sodium iodide; In ethanol; dichloromethane;
DOI:10.1021/ja961640y