(4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone

Base Information

• Chemical Name: (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone
• CAS No.: 335628-11-0
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 335628-11-0.mol

Synonyms:(4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone

Chemical Property of (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone

There total 5 articles about (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone 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:

di-tert-butyl dicarbonate (24424-99-5) + (4S,5R)-5-benzyloxy-4-tert-butyl-2-oxazolidinone (335627-63-9) → (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone (335628-11-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol015535r

Reference yield:

(-)-trans-5-benzyloxy-4-methoxy-2-oxazolidinone (335627-25-3) → (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone (335628-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / BF₃*OEt₂; LiCl; CuCN / tetrahydrofuran / 24 h / -30 °C

2: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; boron trifluoride diethyl etherate; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol015535r

Reference yield:

trans-5-benzyloxy-4-methoxy-2-oxazolidinone → (4S,5R)-5-benzyloxy-3-tert-butoxycarbonyl-4-tert-butyl-2-oxazolidinone (335628-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 49 percent / NaH / tetrahydrofuran / 12 h / 20 °C

2: 77 percent / LiBH₄ / methanol; tetrahydrofuran / 0 °C

3: 74 percent / BF₃*OEt₂; LiCl; CuCN / tetrahydrofuran / 24 h / -30 °C

4: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium borohydride; boron trifluoride diethyl etherate; sodium hydride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol015535r

upstream raw materials:

di-tert-butyl dicarbonate

(4S,5R)-5-benzyloxy-4-tert-butyl-2-oxazolidinone

(-)-trans-5-benzyloxy-4-methoxy-2-oxazolidinone

benzyl alcohol

Downstream raw materials:

tert-butyl N-[(1S)-1-formyl-2,2-dimethylpropyl]carbamate