(1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one

Base Information

• Chemical Name: (1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one
• CAS No.: 113453-64-8
• Molecular Formula: C₄₃H₇₀N₂O₇
• Molecular Weight: 727.038
• Mol file: 113453-64-8.mol

Synonyms:

Chemical Property of (1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one

There total 1 articles about (1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-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:

(4S)-2-bromo-4,6-dimethyl-1,5-heptadiene (113453-48-8) + <6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran (113453-62-6) + <αR,2S,5S>-N-methoxy-α-(1-methoxy-1-methylethyl)-N,5-dimethyl-5-<1-(dimethylhydrazino)propyl>tetrahydro-2-furanacetamide (113453-55-7) → (1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one (113453-64-8,113531-37-6) + (1R,5S)-1-[(2S,5S,2'S,3'S,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/ja00216a026

Reference yield: 88.0%

(1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one (113453-64-8,113531-37-6) → <1R,1(2S,5S,5(2R,3R,5S,5(2S,3R,6R))),5S>-1-<5-<5-<2-ethyl-3-methyl-3-(phenylmethoxy)tetrahydropyran-2-yl>-2-hydroxy-3,5-dimethyltetrahydrofuran-2-yl>-5-methyltetrahydrofuran-2-yl>-1-hydroxy-5,7-dimethyl-3-methylene-6-octen-2-one (113453-65-9)

Guidance literature:

With sodium hydrogen sulfate; In dichloromethane; pentane; for 7h; Ambient temperature;

DOI:10.1021/ja00216a026

Reference yield:

(1R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-(N',N'-dimethyl-hydrazino)-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-(1-methoxy-1-methyl-ethoxy)-5,7-dimethyl-3-methylene-oct-6-en-2-one (113453-64-8,113531-37-6) → <1R,1(2S,5S,5(2R,3R,5S,5(2S,3R,6R))),3R,5S>-1-<5-<5-<2-ethyl-3-methyl-3-(phenylmethoxy)tetrahydropyran-2-yl>-2-hydroxy-3,5-dimethyltetrahydrofuran-2-yl>-5-methyltetrahydrofuran-2-yl>-1-hydroxy-3,5,7-trimethyl-6-octen-2-one

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 1N aq. NaHSO₄ / pentane; CH₂Cl₂ / 7 h / Ambient temperature

2: 90 percent / H₂, i-Pr₂EtN / (Ph₃P)3RhCl / toluene / 4.5 h / 760 Torr

With sodium hydrogen sulfate; hydrogen; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In dichloromethane; toluene; pentane;

DOI:10.1021/ja00216a026

upstream raw materials:

(4S)-2-bromo-4,6-dimethyl-1,5-heptadiene

<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

<αR,2S,5S>-N-methoxy-α-(1-methoxy-1-methylethyl)-N,5-dimethyl-5-<1-(dimethylhydrazino)propyl>tetrahydro-2-furanacetamide

Downstream raw materials:

<1R,1(2S,5S,5(2R,3R,5S,5(2S,3R,6R))),5S>-1-<5-<5-<2-ethyl-3-methyl-3-(phenylmethoxy)tetrahydropyran-2-yl>-2-hydroxy-3,5-dimethyltetrahydrofuran-2-yl>-5-methyltetrahydrofuran-2-yl>-1-hydroxy-5,7-dimethyl-3-methylene-6-octen-2-one

(1R,3R,5S)-1-[(2S,5S,2'R,3'R,5'S)-5'-((2R,5R,6S)-5-Benzyloxy-6-ethyl-5-methyl-tetrahydro-pyran-2-yl)-2'-methoxy-2,3',5'-trimethyl-octahydro-[2,2']bifuranyl-5-yl]-1-hydroxy-3,5,7-trimethyl-oct-6-en-2-one

<2S,4R,6R,6(2S,5S,5(2R,3R,5S,5(2S,3R,6R)))>-6-<5-<5-<2-ethyl-3-methyl-3-(phenylmethoxy)tetrahydropyran-2-yl>-2-methoxy-3,5-dimethyltetrahydrofuran-2-yl>-5-methyltetrahydrofuran-2-yl>-2,4-dimethyl-5-oxo-6-<(phenylmethoxy)methoxy>hexanal

<1R,1(2S,5S,5(2R,3R,5S,5(2S,3R,6R))),3R,5S>-1-<5-<5-<2-ethyl-3-methyl-3-(phenylmethoxy)tetrahydropyran-2-yl>-2-methoxy-3,5-dimethyltetrahydrofuran-2-yl>-5-methyltetrahydrofuran-2-yl>-1-hydroxy-3,5,7-trimethyl-1-<(phenylmethoxy)methoxy>-6-octen-2-one