(2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester

Base Information

• Chemical Name: (2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester
• CAS No.: 856682-14-9
• Molecular Formula: C₃₅H₃₉NO₈
• Molecular Weight: 601.697
• Mol file: 856682-14-9.mol

Synonyms:(2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester

Chemical Property of (2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester

There total 1 articles about (2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl 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: 90.0%

2-benzyloxy-5-(4-methoxy-benzyl)-4-oxo-6a-phenylselanylmethyl-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester → (2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester (856682-14-9)

Guidance literature:

With n-butyl tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; at 100 ℃; for 2h;

Reference yield: 85.0%

(2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester (856682-14-9) → (2R,3aR,6R,6aS)-2-Benzyloxy-6-hydroxymethyl-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester (856682-15-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20 ℃; for 6h;

DOI:10.1021/ja0522783

Reference yield:

(2R,3aR,6S,6aS)-2-Benzyloxy-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6,6-dicarboxylic acid benzyl ester tert-butyl ester (856682-14-9) → salinosporamide A (437742-34-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / NaBH₄ / tetrahydrofuran; ethanol / 6 h / 20 °C

2: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

3: 88 percent / tetrahydrofuran; hexane / 3 h / -78 °C

4: 90 percent / CAN / H₂O; acetonitrile / 6 h / 0 °C

5: liq. NH₃; Na / tetrahydrofuran / 2 h / -78 °C

6: 70.0 mg / NaBH₄ / tetrahydrofuran; H₂O / 0.5 h

7: BCl₃ / CH₂Cl₂ / 0.5 h / 0 °C

8: BOPCl; TEA / CH₂Cl₂ / 16 h / 20 °C

9: 6.8 mg / PH₃PCl₂ / pyridine; acetonitrile / 4 h / 20 °C

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; TEA; ammonia; sodium; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; boron trichloride; dichlorotriphenyl-λ⁴-phosphane; Dess-Martin periodane; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; water; acetonitrile;

DOI:10.1021/ja0522783

Downstream raw materials:

(2R,3aR,6R,6aS)-2-Benzyloxy-6-hydroxymethyl-5-(4-methoxy-benzyl)-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

NPI-2077

(3aR,6R,6aS)-6-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-hydroxy-6a-methyl-4-oxo-hexahydro-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

(2R,3S,4R)-2-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-3-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester