<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

Base Information

Chemical Name:<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene
CAS No.:175356-53-3
Molecular Formula:C₄₃H₇₀O₅Si₂
Molecular Weight:723.197
Hs Code.:

<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8-<tetrahydro-3-methoxy-5-methyl-6(2H)-2-pyran-2-yl>-2,6-octadiene

Synonyms:<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

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Chemical Property of <2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

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Technology Process of <2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

There total 25 articles about <2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene 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: 84.0%

: <2α(2Z,4S,5R,6E,8S),3β,5α,6β>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropyl-siloxy-8--2,6-octadiene

: 175356-53-3
<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

Guidance literature:: With hydrogen fluoride; In tetrahydrofuran; acetonitrile; Ambient temperature;
DOI:10.1021/jo00030a007

Reference yield:

: 95481-54-2
<4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

: 175356-53-3
<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

Guidance literature:: Multi-step reaction with 21 steps

1: 95 percent / Br₂, H₂O / acetonitrile / 1 h / -20 °C

2: 51 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

3: 1.) copper iodide, 2.) chlorotrimethylsilane / 1.) Et₂O, THF, 0 deg C, 20 min, 2.) Et₂O, THF, -78 deg C, 30 min

4: 1.) NaBH₄, 2.) camphorsulfonic acid / 1.) EtOH, THF, -20 deg C, 1.5 h, 2.) EtOH, THF, -20 deg C, 15 min

5: 80 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / 0 °C

6: 73 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 22 h / Ambient temperature

7: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

8: 99 percent / NaOH / methanol; tetrahydrofuran / 0.25 h / Ambient temperature

9: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

10: 99 percent / aq. trifluoroacetic acid / tetrahydrofuran / 2 h / 0 °C

11: 87 percent / tetrapropylammonium perruthenate (VII), 4-methylmorpholine N-oxide monohydrate, 4A molecular sieves / CH₂Cl₂; acetonitrile / 0.75 h / Ambient temperature

12: 1.) s-BuLi / 1.) cyclohexane, THF, -78 deg C, 0.5 h, 2.) cyclohexane, THF, -20 deg C, 1 h

13: trifluoroacetic acid / tetrahydrofuran / 1 h / 0 °C

14: 1.) di-n-butylborontriflate, Et₃N, 3.) phosphate buffer, hydrogen peroxide

15: 1.) AlMe₃, 3.) 1 M aq. tartaric acid

16: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

17: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - -50 °C

18: 1.) potassium hexamethyldisilazane, 18-crown-6 / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, -50 deg C to -40 deg C, 1 h

19: 98 percent / DIBAL-H / hexane; tetrahydrofuran / 0.67 h / -20 °C

20: 93 percent / dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

21: 48percent aq. HF / tetrahydrofuran; acetonitrile / 36 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; phosphate buffer; tetrapropylammonium perruthennate; potassium hexamethyldisilazane; 18-crown-6 ether; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen fluoride; water; dihydrogen peroxide; bromine; trimethylaluminum; sec.-butyllithium; potassium hydride; diisobutylaluminium hydride; tartaric acid; 4-methylmorpholine 4-oxide monohydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1016/0040-4020(95)01107-2

Reference yield:

: (4R,5S)-3-[(R)-2-((R)-6-Hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 175356-53-3
<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

Guidance literature:: Multi-step reaction with 20 steps

1: 51 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

2: 1.) copper iodide, 2.) chlorotrimethylsilane / 1.) Et₂O, THF, 0 deg C, 20 min, 2.) Et₂O, THF, -78 deg C, 30 min

3: 1.) NaBH₄, 2.) camphorsulfonic acid / 1.) EtOH, THF, -20 deg C, 1.5 h, 2.) EtOH, THF, -20 deg C, 15 min

4: 80 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / 0 °C

5: 73 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 22 h / Ambient temperature

6: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

7: 99 percent / NaOH / methanol; tetrahydrofuran / 0.25 h / Ambient temperature

8: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

9: 99 percent / aq. trifluoroacetic acid / tetrahydrofuran / 2 h / 0 °C

10: 87 percent / tetrapropylammonium perruthenate (VII), 4-methylmorpholine N-oxide monohydrate, 4A molecular sieves / CH₂Cl₂; acetonitrile / 0.75 h / Ambient temperature

11: 1.) s-BuLi / 1.) cyclohexane, THF, -78 deg C, 0.5 h, 2.) cyclohexane, THF, -20 deg C, 1 h

12: trifluoroacetic acid / tetrahydrofuran / 1 h / 0 °C

13: 1.) di-n-butylborontriflate, Et₃N, 3.) phosphate buffer, hydrogen peroxide

14: 1.) AlMe₃, 3.) 1 M aq. tartaric acid

15: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

16: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - -50 °C

17: 1.) potassium hexamethyldisilazane, 18-crown-6 / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, -50 deg C to -40 deg C, 1 h

18: 98 percent / DIBAL-H / hexane; tetrahydrofuran / 0.67 h / -20 °C

19: 93 percent / dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

20: 48percent aq. HF / tetrahydrofuran; acetonitrile / 36 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; phosphate buffer; tetrapropylammonium perruthennate; potassium hexamethyldisilazane; 18-crown-6 ether; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen fluoride; dihydrogen peroxide; trimethylaluminum; sec.-butyllithium; potassium hydride; diisobutylaluminium hydride; tartaric acid; 4-methylmorpholine 4-oxide monohydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1016/0040-4020(95)01107-2