(2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

Base Information

Chemical Name:(2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol
CAS No.:155433-56-0
Molecular Formula:C₂₈H₄₀O₇
Molecular Weight:488.621
Hs Code.:

(2R,3R,4R,5R,8S)-8-<m-(benzyloxymethoxy)phenyl>-5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

There total 14 articles about (2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-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:

: 3587-60-8
Benzyloxymethyl chloride

: 155433-56-0
(2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

Guidance literature:: Multi-step reaction with 9 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: 1.) methylmagnesium bromide / 2.) CuI / 1.) THF, 0 deg C, 5 min.; 2.) THF, -20 deg C, 10 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (-)-diisopropyl tartrate; MS 4 Angstroem; methylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 14755-02-3,588-30-7
3-hydroxy-trans-cinnamic acid

: 155433-56-0
(2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

Guidance literature:: Multi-step reaction with 9 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: 1.) methylmagnesium bromide / 2.) CuI / 1.) THF, 0 deg C, 5 min.; 2.) THF, -20 deg C, 10 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (-)-diisopropyl tartrate; MS 4 Angstroem; methylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 74243-89-3
*R^*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol

: 155433-56-0
(2R,3R,4R,5R,8S)-8--5-hydroxymethyl-1,2-isopropylidene-dioxy-8-methoxy-3-methyloctan-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.75 h / -78 °C

2: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C

3: 96 percent / diisobutyl aluminum hydride / hexane; CH₂Cl₂ / 1 h / -78 °C

4: 82 percent / (+)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide / CH₂Cl₂; toluene / 11 h / -20 °C

5: 1.) methylmagnesium bromide / 2.) CuI / 1.) THF, 0 deg C, 5 min.; 2.) THF, -20 deg C, 10 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; methylmagnesium bromide; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)81547-7