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

Base Information

• Chemical Name: Benzoic acid (2R,4R)-6-acetoxy-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 103577-07-7
• Molecular Formula: C₂₁H₃₀O₇
• Molecular Weight: 394.465

Synonyms:

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

There total 17 articles about Benzoic acid (2R,4R)-6-acetoxy-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:

(S)-3,5,6-Trihydroxy-2,2-dimethyl-hexanoic acid ethyl ester → Benzoic acid (2R,4R)-6-acetoxy-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (103577-07-7,103577-11-3,105929-12-2)

Guidance literature:

Multi-step reaction with 16 steps

1: Imidazole / dimethylformamide

2: CSA / benzene / 72percent overall yield from INO 660

3: PPTS / CH₂Cl₂

4: LDA / tetrahydrofuran / -78 °C

5: CSA / CH₂Cl₂; methanol / 38percent yield from INO 690; yield of byproduct (INO 760): 37percent from INO 690

6: PCC, 3A-MS / CH₂Cl₂

7: L-Selectride / tetrahydrofuran / -78 °C / 90percent yield from INO 760

8: 83 percent / BF₃:Et₂O / -30 °C

9: 83 percent / Silica gel / diethyl ether

10: DIBAH / toluene / -78 °C

11: 88 percent / i-Pr₂NEt / CH₂Cl₂ / Heating; 88percent yield from INO 820

12: 87 percent / NBS, AgNO₃, Na₂CO₃ / H₂O; acetonitrile

13: 98 percent / LiAlH₄ / diethyl ether / 0 °C

14: 100 percent / Pyridine

15: 6N HCl / tetrahydrofuran / 50 °C

16: Pyridine / 86percent yield from INO 890

With pyridine; 1H-imidazole; hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; silica gel; L-Selectride; diisobutylaluminium hydride; sodium carbonate; silver nitrate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99027-0

Reference yield:

4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethyl-butyric acid ethyl ester (103577-08-8,103602-41-1,105929-10-0) → Benzoic acid (2R,4R)-6-acetoxy-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (103577-07-7,103577-11-3,105929-12-2)

Guidance literature:

Multi-step reaction with 17 steps

1: p-TsOH / methanol

2: Imidazole / dimethylformamide

3: CSA / benzene / 72percent overall yield from INO 660

4: PPTS / CH₂Cl₂

5: LDA / tetrahydrofuran / -78 °C

6: CSA / CH₂Cl₂; methanol / 38percent yield from INO 690; yield of byproduct (INO 760): 37percent from INO 690

7: PCC, 3A-MS / CH₂Cl₂

8: L-Selectride / tetrahydrofuran / -78 °C / 90percent yield from INO 760

9: 83 percent / BF₃:Et₂O / -30 °C

10: 83 percent / Silica gel / diethyl ether

11: DIBAH / toluene / -78 °C

12: 88 percent / i-Pr₂NEt / CH₂Cl₂ / Heating; 88percent yield from INO 820

13: 87 percent / NBS, AgNO₃, Na₂CO₃ / H₂O; acetonitrile

14: 98 percent / LiAlH₄ / diethyl ether / 0 °C

15: 100 percent / Pyridine

16: 6N HCl / tetrahydrofuran / 50 °C

17: Pyridine / 86percent yield from INO 890

With pyridine; 1H-imidazole; hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; silica gel; L-Selectride; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; silver nitrate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99027-0

Reference yield:

(S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2,2-dimethyl-hexanoic acid ethyl ester → Benzoic acid (2R,4R)-6-acetoxy-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester (103577-07-7,103577-11-3,105929-12-2)

Guidance literature:

Multi-step reaction with 15 steps

1: CSA / benzene / 72percent overall yield from INO 660

2: PPTS / CH₂Cl₂

3: LDA / tetrahydrofuran / -78 °C

4: CSA / CH₂Cl₂; methanol / 38percent yield from INO 690; yield of byproduct (INO 760): 37percent from INO 690

5: PCC, 3A-MS / CH₂Cl₂

6: L-Selectride / tetrahydrofuran / -78 °C / 90percent yield from INO 760

7: 83 percent / BF₃:Et₂O / -30 °C

8: 83 percent / Silica gel / diethyl ether

9: DIBAH / toluene / -78 °C

10: 88 percent / i-Pr₂NEt / CH₂Cl₂ / Heating; 88percent yield from INO 820

11: 87 percent / NBS, AgNO₃, Na₂CO₃ / H₂O; acetonitrile

12: 98 percent / LiAlH₄ / diethyl ether / 0 °C

13: 100 percent / Pyridine

14: 6N HCl / tetrahydrofuran / 50 °C

15: Pyridine / 86percent yield from INO 890

With pyridine; hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; silica gel; L-Selectride; diisobutylaluminium hydride; sodium carbonate; silver nitrate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99027-0

upstream raw materials:

acetic anhydride

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

(7R,9R)-9-((S)-2,3-Dimethoxy-propyl)-10,10-dimethyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-ol

4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethyl-butyric acid ethyl ester

Downstream raw materials:

(+)-benzoylpedamide

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

(2R,4R,6S)-4-benzoyloxy-6-cyano-2-<(2S)-2,3-dimethoxypropyl>-3,3-dimethyl-2H-tetrahydropyran

(2R,4R,6R)-4-benzoyloxy-6-cyano-2-<(2S)-2,3-dimethoxypropyl>-3,3-dimethyl-2H-tetrahydropyran

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