(R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

Base Information

• Chemical Name: (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine
• CAS No.: 135638-41-4
• Molecular Formula: C₂₂H₃₀N₂O₇
• Molecular Weight: 434.489
• Mol file: 135638-41-4.mol

Synonyms:(R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

Chemical Property of (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

There total 21 articles about (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine 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: 82.0%

benzyl (S)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (134038-74-7) + trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1) → (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine (135638-41-4)

Guidance literature:

With potassium tert-butylate; In dichloromethane; at -60 - 20 ℃; for 12h;

DOI:10.1039/c39910000275

Reference yield:

(S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol (135582-93-3) → (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine (135638-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 79 percent / Et₂O*BF₃ / acetone / 24 h / Ambient temperature

3: 92 percent / 1 N aq. LiOH / tetrahydrofuran / 1 h / Ambient temperature

4: 62 percent / DCC, DMSO, dichloroacetic acid / benzene / 2 h / 0 - 20 °C

5: 1) KOBu-t / 1) CH₂Cl₂, -70 deg C, 15 min, 2) a) -70 deg C, 0.5 h, b) to room temperature, overnight

With pyridine; dichloro-acetic acid; lithium hydroxide; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1055/s-1991-26480

Reference yield:

benzyl (S)-5-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (134038-73-6) → (R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine (135638-41-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / DCC, DMSO, dichloroacetic acid / benzene / 2 h / 0 - 20 °C

2: 1) KOBu-t / 1) CH₂Cl₂, -70 deg C, 15 min, 2) a) -70 deg C, 0.5 h, b) to room temperature, overnight

With dichloro-acetic acid; potassium tert-butylate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In benzene;

DOI:10.1055/s-1991-26480

upstream raw materials:

benzyl (S)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

(S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol

benzyl (S)-5-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(R)-3-benzyloxycarbonyl-5-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(R)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(S)-N-tert-butoxycarbonylalanin-3-yl>-2,2-dimethyl-1,3-oxazolidine