(S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester

Base Information

• Chemical Name: (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester
• CAS No.: 1026295-28-2
• Molecular Formula: C₁₅H₁₇F₂NO₆
• Molecular Weight: 345.3
• Mol file: 1026295-28-2.mol

Synonyms:

Chemical Property of (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester

There total 9 articles about (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl 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:

(S)-4-Benzyloxycarbonylamino-2,2-difluoro-5-hydroxy-pentanoic acid ethyl ester → (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester (1026295-28-2)

Guidance literature:

With chromium(VI) oxide; water; periodic acid; In acetonitrile; at 0 ℃; for 0.333333h;

DOI:10.1055/s-2002-35616

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester (1026295-28-2)

Guidance literature:

Multi-step reaction with 8 steps

1: BF₃*Et₂O / acetone

2: NaBH₄ / tetrahydrofuran; methanol

3: 87 percent / aq. NaClO; TEMPO; NaBr / ethyl acetate; toluene / 0.25 h / 0 °C

4: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

5: tetrahydrofuran / 48 h / 30 - 40 °C

6: 200 mg / Et₃SiH; benzoyl peroxide / dioxane / Heating

7: p-TsOH*H₂O / ethanol / Heating

8: H₅IO₆; CrO₃; H₂O / acetonitrile / 0.33 h / 0 °C

With chromium(VI) oxide; triethylsilane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; boron trifluoride diethyl etherate; water; toluene-4-sulfonic acid; periodic acid; sodium bromide; zinc; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; ethyl acetate; acetone; toluene; acetonitrile; 4: Reformatsky reaction;

DOI:10.1055/s-2002-35616

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → (S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester (1026295-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

2: tetrahydrofuran / 48 h / 30 - 40 °C

3: 200 mg / Et₃SiH; benzoyl peroxide / dioxane / Heating

4: p-TsOH*H₂O / ethanol / Heating

5: H₅IO₆; CrO₃; H₂O / acetonitrile / 0.33 h / 0 °C

With chromium(VI) oxide; triethylsilane; water; toluene-4-sulfonic acid; periodic acid; zinc; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; acetonitrile; 1: Reformatsky reaction;

DOI:10.1055/s-2002-35616

upstream raw materials:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

benzyl chloroformate

(S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester