(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

Base Information

Chemical Name:(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester
CAS No.:221007-85-8
Molecular Formula:C₂₆H₄₀O₆
Molecular Weight:448.6
Hs Code.:

Synonyms:(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

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Chemical Property of (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

Chemical Property:

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Technology Process of (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

There total 8 articles about (2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester 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: 80.0%

: 870-63-3
prenyl bromide

: 221007-84-7
2,4,6-trideoxy-2,4-dimethyl-7,8-O-(1-methylethylidene)-5-O-(phenylmethyl)-D-glycero-D-gluco-octanoic acid methyl ester

: 221007-85-8
(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1021/jo981310r

Reference yield:

: 32233-43-5
2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

: 221007-85-8
(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 4 Angstroem molecular sieves / toluene / -78 °C

3: 83 percent / NaH, Bu₄NI / tetrahydrofuran; dimethylformamide / 3 h / 23 °C

4: 1.) O₃, Sudan Red, 2.) Ph₃P / CH₂Cl₂ / -78 - 22 °C

5: 9.30 g / Bu₂BOTf, i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

6: aq. H₂O₂, LiOH / tetrahydrofuran / 0 °C

7: diethyl ether / 5 h

8: 80 percent / NaN(TMS)2 / tetrahydrofuran / -78 - 0 °C

With lithium hydroxide; oxalyl dichloride; 4 A molecular sieve; sudan red; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981310r

Reference yield:

: 32233-44-6
2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

: 221007-85-8
(2S)-2,4,6-trideoxy-2,4-dimethyl-2-(3-methyl-2-butenyl)-7,8-O-(1-methylethylidene)-D-altro-octonic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 4 Angstroem molecular sieves / toluene / -78 °C

2: 83 percent / NaH, Bu₄NI / tetrahydrofuran; dimethylformamide / 3 h / 23 °C

3: 1.) O₃, Sudan Red, 2.) Ph₃P / CH₂Cl₂ / -78 - 22 °C

4: 9.30 g / Bu₂BOTf, i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

5: aq. H₂O₂, LiOH / tetrahydrofuran / 0 °C

6: diethyl ether / 5 h

7: 80 percent / NaN(TMS)2 / tetrahydrofuran / -78 - 0 °C

With lithium hydroxide; 4 A molecular sieve; sudan red; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981310r