(2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine
• CAS No.: 199998-81-7
• Molecular Formula: C₂₂H₂₇NO₁₁S
• Molecular Weight: 513.522
• Mol file: 199998-81-7.mol

Synonyms:(2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine

Chemical Property of (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine

There total 6 articles about (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine 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: 77.0%

cycl-isopropylidene malonate (2033-24-1) + (2S,4R)-1-benzyloxycarbonyl-2-(carboxymethyloxymethyl)-4-methanesulfonyloxypyrrolidine (117811-80-0) → (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine (199998-81-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine (199998-81-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / ethyl acetate / 0.5 h / 0 - 5 °C

2: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

3: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

4: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

5: 77 percent / DMAP, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine (199998-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

2: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

3: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

4: 77 percent / DMAP, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

cycl-isopropylidene malonate

(2S,4R)-1-benzyloxycarbonyl-2-(carboxymethyloxymethyl)-4-methanesulfonyloxypyrrolidine

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

Downstream raw materials:

(2S,4R)-1-benzyloxycarbonyl-2-(2-oxopropyl)oxymethyl-4-methanesulfonyloxypyrrolidine

(2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxypropyl)oxymethyl-4-methanesulfonyloxypyrrolidine

(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoropropyl)oxymethyl4-methanesulfonyloxypyrrolidine