threo aldol

Base Information

Chemical Name:threo aldol
CAS No.:114673-25-5
Molecular Formula:C₃₂H₅₀O₉
Molecular Weight:578.744
Hs Code.:

Synonyms:threo aldol

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Chemical Property of threo aldol

Chemical Property:

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Technology Process of threo aldol

There total 18 articles about threo aldol 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: 12.0%

: 106734-82-1
<4S<4α(R*),5β,6α(1R*,2S*)>>-6-<4-(1,3-dioxolan-2-yl)-1-methyl-2-<(phenylmethoxy)methoxy>butyl>-α,2,2,5-tetramethyl-1,3-dioxane-4-acetaldehyde

: 83416-30-2
tert-Butyl-[(E)-1-((E)-2-methoxy-vinyl)-propenyloxy]-dimethyl-silane

: 106734-84-3
<4R<4α,5β,6α(1S*,2R*)>>-2-<1-<6-<4-(1,3-dioxolan-2-yl)-1-methyl-2-<(phenylmethoxy)methoxy>butyl>-2,2,5-trimethyl-1,3-dioxan-4-yl>ethyl>-2,3-dihydro-3-methyl-4H-pyran-4-one

: erythro aldol

: 114673-25-5
threo aldol

Guidance literature:: With boron trifluoride diethyl etherate; In various solvent(s); at -78 ℃; for 0.05h;
DOI:10.1021/ja00221a043

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 114673-25-5
threo aldol

Guidance literature:: Multi-step reaction with 15 steps

1: 91 percent / diisopropylamine / 16 h / Ambient temperature

2: 1.) ozone, sodium bicarbonate; 2.) dimethyl sulfide, Zn, AcOH / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 20 min; 2.) room temp.

3: 80 percent / MgBr₂*OEt₂ / CH₂Cl₂; diethyl ether; benzene / 5 h / -65 deg C then to 0 deg C

4: CeCl₃*7H₂O, NaBH₄ / ethanol; CH₂Cl₂ / -78 °C

5: p-TsOH / benzene / 1 h / Ambient temperature

6: 1.) BH₃*DMS; 2.) H₂O₂, NaOH / 1.) THF, 0 deg C then to room temp. over 8 h; 2.) room temp., 12 h

7: 84 percent / oxallyl chloride, DMSO, triethylamine / CH₂Cl₂ / 0.25 h

8: 88 percent / lithium tri-sec-butyl borohydride / tetrahydrofuran / -78 deg C, 0.5 h then to -30 deg C

9: 80 percent / DDQ / CH₂Cl₂; H₂O / 4.5 h / Ambient temperature

10: 82 percent / lithium borohydride / tetrahydrofuran / 16 h / Ambient temperature

11: 95 percent / imidazole / dimethylformamide / 2 h

12: 99 percent / camphorsulfonic acid, triethylamine / 1.5 h

13: 100 percent / tetra-n-butylammonium fluoride / dimethylformamide; tetrahydrofuran / 5 h / Ambient temperature

14: 92 percent / tetra-n-butylammonium fluoride / dimethylformamide; tetrahydrofuran / 5 h / Ambient temperature

15: 50 percent / BF₃*OEt₂ / various solvent(s) / 0.05 h / -78 °C

With oxallyl chloride; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; dimethylsulfide; dimethylsulfide borane complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00221a043

Reference yield:

: 37610-80-3
1,3-dioxolan-2-ylethylmagnesium bromide

: 114673-25-5
threo aldol

Guidance literature:: Multi-step reaction with 17 steps

1: 90 percent / tetrahydrofuran / -78 deg C then 0 deg C

2: 74 percent / sodium hydride / tetrahydrofuran; hexamethylphosphoric acid triamide / 22 h / Ambient temperature

3: 91 percent / diisopropylamine / 16 h / Ambient temperature

4: 1.) ozone, sodium bicarbonate; 2.) dimethyl sulfide, Zn, AcOH / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 20 min; 2.) room temp.

5: 80 percent / MgBr₂*OEt₂ / CH₂Cl₂; diethyl ether; benzene / 5 h / -65 deg C then to 0 deg C

6: CeCl₃*7H₂O, NaBH₄ / ethanol; CH₂Cl₂ / -78 °C

7: p-TsOH / benzene / 1 h / Ambient temperature

8: 1.) BH₃*DMS; 2.) H₂O₂, NaOH / 1.) THF, 0 deg C then to room temp. over 8 h; 2.) room temp., 12 h

9: 84 percent / oxallyl chloride, DMSO, triethylamine / CH₂Cl₂ / 0.25 h

10: 88 percent / lithium tri-sec-butyl borohydride / tetrahydrofuran / -78 deg C, 0.5 h then to -30 deg C

11: 80 percent / DDQ / CH₂Cl₂; H₂O / 4.5 h / Ambient temperature

12: 82 percent / lithium borohydride / tetrahydrofuran / 16 h / Ambient temperature

13: 95 percent / imidazole / dimethylformamide / 2 h

14: 99 percent / camphorsulfonic acid, triethylamine / 1.5 h

15: 100 percent / tetra-n-butylammonium fluoride / dimethylformamide; tetrahydrofuran / 5 h / Ambient temperature

16: 92 percent / tetra-n-butylammonium fluoride / dimethylformamide; tetrahydrofuran / 5 h / Ambient temperature

17: 50 percent / BF₃*OEt₂ / various solvent(s) / 0.05 h / -78 °C

With oxallyl chloride; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; dimethylsulfide; dimethylsulfide borane complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; L-Selectride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; zinc; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00221a043