(E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester
• CAS No.: 123060-82-2
• Molecular Formula: C₂₆H₃₆O₆
• Molecular Weight: 444.568

Synonyms:

Chemical Property of (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester

There total 38 articles about (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic 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: 80.0%

(R)-2-((1S,2S,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-propionaldehyde (123060-81-1,123123-11-5) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester (123060-82-2,123123-12-6)

Guidance literature:

In 1,2-dichloro-ethane; at 50 ℃;

DOI:10.1016/S0040-4039(00)82235-2

Reference yield:

benzyl bromide (100-39-0) → (E)-(R)-4-((1R,2S,3aS,4R,5S,7aS,8R)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester (123060-82-2,123123-12-6)

Guidance literature:

Multi-step reaction with 17 steps

1: NaH

2: L-selectride / tetrahydrofuran / -78 °C

3: dL-CSA

4: LiAlH₄ / tetrahydrofuran / Ambient temperature

5: 1.) DMSO, (COCl)2, 2.) Et₃N, / 1.) -78 deg C,

6: tetrahydrofuran / 0 °C

7: AcOH / H₂O / 40 °C

8: benzene / 50 °C

9: PCC

10: i-Pr₂NEt / 1,2-dichloro-ethane / 55 °C

11: t-BuOK / tetrahydrofuran / -78 °C

12: 1.) HCl, 2.) dl-CSA, / 1.) MeOH, room temp; 2.) PhH, 50 deg C,

13: L-selectride / tetrahydrofuran / -78 °C

14: i-Pr₂NEt

15: 1.) LDA, / 1.) THF,

16: Dibal-H / tetrahydrofuran / -78 °C

17: 1,2-dichloro-ethane / 50 °C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; DL-10-camphorsulfonic acid; potassium tert-butylate; L-Selectride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; water; 1,2-dichloro-ethane; benzene;

DOI:10.1016/S0040-4039(00)82235-2

Reference yield:

benzyl bromide (100-39-0) → (E)-(S)-4-((1S,2R,3aR,4S,5R,7aR,8S)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-pent-2-enoic acid methyl ester (123060-82-2,123123-12-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 53 percent / NaH

2: 95 percent / L-selectride / tetrahydrofuran / -78 °C

3: 98 percent / dl-CSA

4: 99 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

5: 1.) DMSO, (COCl)2, 2.) Et₃N, / 1.) -78 deg C,

6: 65 percent / tetrahydrofuran / 0 °C

7: 67 percent / AcOH / H₂O / 40 °C

8: 77 percent / benzene / 50 °C

9: 79 percent / PCC, 4A molecular sieves,

10: 91 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 55 °C

11: 99 percent / t-BuOK / tetrahydrofuran / -78 °C

12: 1.) HCl, 2.) dl-CSA, / 1.) MeOH, room temp; 2.) PhH, 50 deg C,

13: 98 percent / L-selectride / tetrahydrofuran / -78 °C

14: 98 percent / i-Pr₂NEt

15: 1.) LDA, / 1.) THF

16: 98 percent / Dibal-H / tetrahydrofuran / -78 °C

17: 80 percent / 1,2-dichloro-ethane / 50 °C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; DL-10-camphorsulfonic acid; 4 A molecular sieve; potassium tert-butylate; L-Selectride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; water; 1,2-dichloro-ethane; benzene;

DOI:10.1016/S0040-4039(00)82235-2

upstream raw materials:

(S)-2-((1R,2R,3aS,4R,5S,7aS,8R)-4-Benzyloxymethyl-7a-hydroxy-8-methoxymethoxy-octahydro-1,5-methano-inden-2-yl)-propionaldehyde

methyl (triphenylphosphoranylidene)acetate

benzyl bromide

(1R,2S,3R,4S)-3-Hydroxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Downstream raw materials:

(1R,5R,6S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-one

(1S,5S,6R)-5-((R)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-bicyclo[4.3.1]dec-2-en-7-one

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