Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester

Base Information

• Chemical Name: Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester
• CAS No.: 122131-36-6
• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.531
• Mol file: 122131-36-6.mol

Synonyms:Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester

Chemical Property of Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester

There total 21 articles about Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl 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:

benzyl bromide (100-39-0) → Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester (122131-36-6)

Guidance literature:

Multi-step reaction with 18 steps

2: 92 percent / LDA / tetrahydrofuran / 0.04 h / -78 °C

3: 75 percent / 1) LDA, 2) CF₃COOH / tetrahydrofuran / -78 °C

4: 83 percent / LiAlH₄ / tetrahydrofuran / -30 °C

5: 95 percent / pyridine

6: 92 percent / NaH / tetrahydrofuran

7: 1) Zn-Cu, 2) Zn, NH₄Cl / 1) ether, room temperature, 5.5 h; 2) MeOH, 0 deg C

8: 74 percent / methanol / Ambient temperature

9: NaBH₄ / methanol

10: 1) MsCl, pyridine; 2) t-BuOK / 2) DMSO

11: 89 percent / HgCl₂ / acetonitrile; H₂O / 40 °C

12: TsOH

13: PCC, MS-3A

14: CH₂Cl₂

15: NaBH₄, NiCl₂*6H₂O / methanol

16: 97 percent / LiAlH₄ / diethyl ether

17: TsOH / H₂O; acetone

18: 82 percent / pyridine

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; potassium tert-butylate; copper; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; methanesulfonyl chloride; pyridinium chlorochromate; trifluoroacetic acid; mercury dichloride; nickel dichloride; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)82126-7

Reference yield:

(3aR,4R,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-4-carboxylic acid (116217-06-2) → Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester (122131-36-6)

Guidance literature:

Multi-step reaction with 18 steps

2: 92 percent / LDA / tetrahydrofuran / 0.04 h / -78 °C

3: 75 percent / 1) LDA, 2) CF₃COOH / tetrahydrofuran / -78 °C

4: 83 percent / LiAlH₄ / tetrahydrofuran / -30 °C

5: 95 percent / pyridine

6: 92 percent / NaH / tetrahydrofuran

7: 1) Zn-Cu, 2) Zn, NH₄Cl / 1) ether, room temperature, 5.5 h; 2) MeOH, 0 deg C

8: 74 percent / methanol / Ambient temperature

9: NaBH₄ / methanol

10: 1) MsCl, pyridine; 2) t-BuOK / 2) DMSO

11: 89 percent / HgCl₂ / acetonitrile; H₂O / 40 °C

12: TsOH

13: PCC, MS-3A

14: CH₂Cl₂

15: NaBH₄, NiCl₂*6H₂O / methanol

16: 97 percent / LiAlH₄ / diethyl ether

17: TsOH / H₂O; acetone

18: 82 percent / pyridine

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; potassium tert-butylate; copper; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; methanesulfonyl chloride; pyridinium chlorochromate; trifluoroacetic acid; mercury dichloride; nickel dichloride; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)82126-7

Reference yield:

methyl cis-6-<2-(dimethylamino)-2-oxoethyl>-3-cyclohexene-1-carboxylate (74320-39-1) → Acetic acid (R)-4-((1S,2R,3S,4S,6S)-4-benzyloxymethyl-2-methoxy-7-oxo-bicyclo[4.2.0]oct-3-yl)-pentyl ester (122131-36-6)

Guidance literature:

Multi-step reaction with 21 steps

1: 1) LiOH, 2) KI₃, aq. NaHCO₃ / 1) aq. MeOH

2: 92 percent / DBU / benzene

3: 1) BF₃*OEt₂, 2) 10percent HCl / 1) CH₂Cl₂; 2) THF, reflux

5: 92 percent / LDA / tetrahydrofuran / 0.04 h / -78 °C

6: 75 percent / 1) LDA, 2) CF₃COOH / tetrahydrofuran / -78 °C

7: 83 percent / LiAlH₄ / tetrahydrofuran / -30 °C

8: 95 percent / pyridine

9: 92 percent / NaH / tetrahydrofuran

10: 1) Zn-Cu, 2) Zn, NH₄Cl / 1) ether, room temperature, 5.5 h; 2) MeOH, 0 deg C

11: 74 percent / methanol / Ambient temperature

12: NaBH₄ / methanol

13: 1) MsCl, pyridine; 2) t-BuOK / 2) DMSO

14: 89 percent / HgCl₂ / acetonitrile; H₂O / 40 °C

15: TsOH

16: PCC, MS-3A

17: CH₂Cl₂

18: NaBH₄, NiCl₂*6H₂O / methanol

19: 97 percent / LiAlH₄ / diethyl ether

20: TsOH / H₂O; acetone

21: 82 percent / pyridine

With pyridine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; potassium triiodide; boron trifluoride diethyl etherate; potassium tert-butylate; copper; sodium hydride; sodium hydrogencarbonate; ammonium chloride; toluene-4-sulfonic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; trifluoroacetic acid; mercury dichloride; nickel dichloride; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)82126-7

upstream raw materials:

benzyl bromide

(3aR,4R,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-4-carboxylic acid

methyl cis-6-<2-(dimethylamino)-2-oxoethyl>-3-cyclohexene-1-carboxylate

N,N-Dimethyl-2-((1S,2R,5R)-7-oxo-6-oxa-bicyclo[3.2.1]oct-3-en-2-yl)-acetamide

Downstream raw materials:

Acetic acid (S)-4-((3aR,4R,5R,6R,7aR)-6-benzyloxymethyl-4-methoxy-2-oxo-octahydro-benzofuran-5-yl)-pentyl ester