(1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester
• CAS No.: 93808-79-8
• Molecular Formula: C₁₅H₂₂O₈
• Molecular Weight: 330.335

Synonyms:

Chemical Property of (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester

There total 29 articles about (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic 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:

Acetic acid (2R,3S,6S)-6-ethoxy-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-yl ester (55735-68-7) → (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester (93808-79-8)

Guidance literature:

Multi-step reaction with 25 steps

1: 70 percent / pyridine / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 89 percent / NaI, Ac₂O / 60 °C

3: 89 percent / AIBN / toluene

4: 100 percent / NEt₃, H₂O / methanol

5: NEt₃ / CH₂Cl₂

6: Bu₃SnCl, NaCNBH₃, AIBN

7: 78 percent / H₂O₂, KHCO₃, KF

9: 1.) O₃, 2.) Me₂S / 1.) MeOH

10: K₂CO₃ / methanol / 24 h

11: KHMDS

12: 78 percent / Bu₂SnO, NBS

13: 88 percent / NaBH(OAc)3 / ethyl acetate

14: 85 percent / NEt₃, DMAP / CH₂Cl₂

15: 82 percent / Ag₂O

16: aq. CH₃COOH / tetrahydrofuran / 12 h / 90 °C

17: BuLi / tetrahydrofuran

18: 95 percent / pyridine

19: (n-Bu)4NF / tetrahydrofuran

20: pyridinium dichromate / dimethylformamide

22: aq. CH₃COOH / tetrahydrofuran / 90 °C

23: pyridinium dichromate / dimethylformamide

25: 1.) O₃, 2.) Me₂S

With pyridine; dmap; potassium fluoride; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; acetic anhydride; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00094a009

Reference yield:

Acetic acid (2S,3S,6S)-6-ethoxy-2-iodomethyl-3,6-dihydro-2H-pyran-3-yl ester (61243-08-1) → (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester (93808-79-8)

Guidance literature:

Multi-step reaction with 23 steps

1: 89 percent / AIBN / toluene

2: 100 percent / NEt₃, H₂O / methanol

3: NEt₃ / CH₂Cl₂

4: Bu₃SnCl, NaCNBH₃, AIBN

5: 78 percent / H₂O₂, KHCO₃, KF

7: 1.) O₃, 2.) Me₂S / 1.) MeOH

8: K₂CO₃ / methanol / 24 h

9: KHMDS

10: 78 percent / Bu₂SnO, NBS

11: 88 percent / NaBH(OAc)3 / ethyl acetate

12: 85 percent / NEt₃, DMAP / CH₂Cl₂

13: 82 percent / Ag₂O

14: aq. CH₃COOH / tetrahydrofuran / 12 h / 90 °C

15: BuLi / tetrahydrofuran

16: 95 percent / pyridine

17: (n-Bu)4NF / tetrahydrofuran

18: pyridinium dichromate / dimethylformamide

20: aq. CH₃COOH / tetrahydrofuran / 90 °C

21: pyridinium dichromate / dimethylformamide

23: 1.) O₃, 2.) Me₂S

With pyridine; dmap; potassium fluoride; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00094a009

Reference yield:

Acetic acid (2R,3S,6S)-6-ethoxy-2-(toluene-4-sulfonyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester (61243-02-5) → (1S,2R,3R,5S,6S)-3-Acetoxy-5-formyl-2-methoxy-6-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester (93808-79-8)

Guidance literature:

Multi-step reaction with 24 steps

1: 89 percent / NaI, Ac₂O / 60 °C

2: 89 percent / AIBN / toluene

3: 100 percent / NEt₃, H₂O / methanol

4: NEt₃ / CH₂Cl₂

5: Bu₃SnCl, NaCNBH₃, AIBN

6: 78 percent / H₂O₂, KHCO₃, KF

8: 1.) O₃, 2.) Me₂S / 1.) MeOH

9: K₂CO₃ / methanol / 24 h

10: KHMDS

11: 78 percent / Bu₂SnO, NBS

12: 88 percent / NaBH(OAc)3 / ethyl acetate

13: 85 percent / NEt₃, DMAP / CH₂Cl₂

14: 82 percent / Ag₂O

15: aq. CH₃COOH / tetrahydrofuran / 12 h / 90 °C

16: BuLi / tetrahydrofuran

17: 95 percent / pyridine

18: (n-Bu)4NF / tetrahydrofuran

19: pyridinium dichromate / dimethylformamide

21: aq. CH₃COOH / tetrahydrofuran / 90 °C

22: pyridinium dichromate / dimethylformamide

24: 1.) O₃, 2.) Me₂S

With pyridine; dmap; potassium fluoride; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; acetic anhydride; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00094a009

upstream raw materials:

(3S,4S,5R,6R,8R)-6-Acetoxy-4-carbomethoxy-5-methoxy-8-vinylcyclohexane acetic acid methyl ester

Acetic acid (2R,3S,6S)-6-ethoxy-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3S,6S)-6-ethoxy-2-iodomethyl-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2R,3S,6S)-6-ethoxy-2-(toluene-4-sulfonyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester

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