Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 85708-36-7
• Molecular Formula: C₂₀H₂₇ClO₆
• Molecular Weight: 398.884
• Mol file: 85708-36-7.mol

Synonyms:Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

There total 18 articles about Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl 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:

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (85708-36-7)

Guidance literature:

Multi-step reaction with 19 steps

1: p-TsOH*H₂O / benzene / 8 h / Heating

2: 64 percent / PCC, NaOAc / CH₂Cl₂ / 12 h / Ambient temperature

3: 2.) Jones reagent / 1.) ether, 12 h at r.t.; 2.) acetone, 30 min at 0 deg C

4: 1.) LiAlH₄; 2.) t-AmONa / 1.) ether, toluene, 2 h at -123 deg C; 2.) DMSO, 2 h at r.t.

5: 99 percent / mCPBA / CH₂Cl₂ / 12 h / Ambient temperature

6: 1.) NaOMe; 2.) Collins reagent / 1.) benzene, 2 d at r.t.; 2.) CH₂Cl₂, 2 h at r.t.

7: 95 percent / LiAlH(OtBu)3 / diethyl ether / 1 h / -78 °C

8: 93 percent / NaH / benzene / 2 h / Heating

9: 92 percent / 3 N HCl / acetone / 5 h / Heating

10: 85 percent / diethyl ether / 12 h / Ambient temperature

11: 73 percent / Na / liquid ammonia / 0.33 h / -78 °C

12: 1.) mCPBA; 2.) p-TsOH*H₂O / 1.) methylene dichloride, r.t., 12 h; 2.) benzene, reflux, 12 h

13: Jones reagent / acetone / 12 h / Ambient temperature

14: 75 percent / diethyl ether

15: 90 percent / NaBH₄ / ethanol / 0.5 h / -78 °C

16: 46 percent / pyridine / 12 h / Ambient temperature

17: 54 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

18: triethylamine / methanol; H₂O / 12 h / Ambient temperature

19: SOCl₂, DMF / CH₂Cl₂ / 3 h / Heating

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; jones reagent; Collins oxidation agent; sodium methylate; sodium acetate; sodium; sodium tert-pentoxide; sodium hydride; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; acetone; benzene;

DOI:10.1016/0040-4020(84)80017-4

Reference yield:

(4R,5R)-4,5-dimethyl-2-(1,1-dimethyl-2-oxoethyl)-1,3-dioxolane (73787-10-7) → Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (85708-36-7)

Guidance literature:

Multi-step reaction with 17 steps

1: 2.) Jones reagent / 1.) ether, 12 h at r.t.; 2.) acetone, 30 min at 0 deg C

2: 1.) LiAlH₄; 2.) t-AmONa / 1.) ether, toluene, 2 h at -123 deg C; 2.) DMSO, 2 h at r.t.

3: 99 percent / mCPBA / CH₂Cl₂ / 12 h / Ambient temperature

4: 1.) NaOMe; 2.) Collins reagent / 1.) benzene, 2 d at r.t.; 2.) CH₂Cl₂, 2 h at r.t.

5: 95 percent / LiAlH(OtBu)3 / diethyl ether / 1 h / -78 °C

6: 93 percent / NaH / benzene / 2 h / Heating

7: 92 percent / 3 N HCl / acetone / 5 h / Heating

8: 85 percent / diethyl ether / 12 h / Ambient temperature

9: 73 percent / Na / liquid ammonia / 0.33 h / -78 °C

10: 1.) mCPBA; 2.) p-TsOH*H₂O / 1.) methylene dichloride, r.t., 12 h; 2.) benzene, reflux, 12 h

11: Jones reagent / acetone / 12 h / Ambient temperature

12: 75 percent / diethyl ether

13: 90 percent / NaBH₄ / ethanol / 0.5 h / -78 °C

14: 46 percent / pyridine / 12 h / Ambient temperature

15: 54 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

16: triethylamine / methanol; H₂O / 12 h / Ambient temperature

17: SOCl₂, DMF / CH₂Cl₂ / 3 h / Heating

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; jones reagent; Collins oxidation agent; sodium methylate; sodium; sodium tert-pentoxide; sodium hydride; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; acetone; benzene;

DOI:10.1016/0040-4020(84)80017-4

Reference yield:

2-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-2-methyl-hex-5-en-3-one (73787-13-0) → Benzoic acid (2R,4R,6S)-6-chlorocarbonyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (85708-36-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) LiAlH₄; 2.) t-AmONa / 1.) ether, toluene, 2 h at -123 deg C; 2.) DMSO, 2 h at r.t.

2: 99 percent / mCPBA / CH₂Cl₂ / 12 h / Ambient temperature

3: 1.) NaOMe; 2.) Collins reagent / 1.) benzene, 2 d at r.t.; 2.) CH₂Cl₂, 2 h at r.t.

4: 95 percent / LiAlH(OtBu)3 / diethyl ether / 1 h / -78 °C

5: 93 percent / NaH / benzene / 2 h / Heating

6: 92 percent / 3 N HCl / acetone / 5 h / Heating

7: 85 percent / diethyl ether / 12 h / Ambient temperature

8: 73 percent / Na / liquid ammonia / 0.33 h / -78 °C

9: 1.) mCPBA; 2.) p-TsOH*H₂O / 1.) methylene dichloride, r.t., 12 h; 2.) benzene, reflux, 12 h

10: Jones reagent / acetone / 12 h / Ambient temperature

11: 75 percent / diethyl ether

12: 90 percent / NaBH₄ / ethanol / 0.5 h / -78 °C

13: 46 percent / pyridine / 12 h / Ambient temperature

14: 54 percent / LDA / tetrahydrofuran / 0.33 h / -78 °C

15: triethylamine / methanol; H₂O / 12 h / Ambient temperature

16: SOCl₂, DMF / CH₂Cl₂ / 3 h / Heating

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; jones reagent; Collins oxidation agent; sodium methylate; sodium; sodium tert-pentoxide; sodium hydride; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; acetone; benzene;

DOI:10.1016/0040-4020(84)80017-4

upstream raw materials:

2,2-dimethyl-3-hydroxypropionaldehyde

(R)-2-((S)-2,3-Dimethoxy-propyl)-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-ol

(6R,8S)-8,9-Dimethoxy-5,5-dimethyl-non-1-ene-4,6-diol

2-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-2-methyl-hex-5-en-3-one

Downstream raw materials:

(+)-benzoylpedamide