(2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine

Base Information

• Chemical Name: (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine
• CAS No.: 132430-75-2
• Molecular Formula: C₂₆H₃₅NO₆
• Molecular Weight: 457.567

Synonyms:(2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine

Chemical Property of (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine

There total 12 articles about (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine 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:

(2Z,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-penten-5-olide (124085-71-8) → (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine (132430-75-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 58 percent / OsO₄, N-methylmorpholine N-oxide*H₂O / acetone; H₂O / Ambient temperature

2: 84 percent / p-TsOH / acetone / Ambient temperature

3: 1.) 2N NaOH / 1.) THF, MeOH, RT, 1h, 2.) ether

4: 83 percent / N,N-diethylaniline / CH₂Cl₂ / 20 h / Ambient temperature

5: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

6: 95 percent / NEt₃ / CH₂Cl₂ / 0.25 h / 0 °C

7: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C

8: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature

9: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N,N-diethylaniline; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.38.2712

Reference yield:

(2RS,4S)-4-<(tert-butoxycarbonyl)amino>-2-phenylseleno-5-pentanolide (132430-61-6,132430-62-7) → (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine (132430-75-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / 30percent H₂O₂ / ethyl acetate / 15 - 20 °C

2: 58 percent / OsO₄, N-methylmorpholine N-oxide*H₂O / acetone; H₂O / Ambient temperature

3: 84 percent / p-TsOH / acetone / Ambient temperature

4: 1.) 2N NaOH / 1.) THF, MeOH, RT, 1h, 2.) ether

5: 83 percent / N,N-diethylaniline / CH₂Cl₂ / 20 h / Ambient temperature

6: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

7: 95 percent / NEt₃ / CH₂Cl₂ / 0.25 h / 0 °C

8: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C

9: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature

10: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; potassium tert-butylate; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N,N-diethylaniline; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1248/cpb.38.2712

Reference yield:

(2S,3S,4R)-2,3-dihydroxy-4-<(tert-butoxycarbonyl)amino>-5-pentanolide (132430-63-8) → (2R,3S,4R)-3,4-bis(benzyloxy)-N-(tert-butoxycarbonyl)-2-<(methoxymethoxy)methyl>pyrrolidine (132430-75-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / p-TsOH / acetone / Ambient temperature

2: 1.) 2N NaOH / 1.) THF, MeOH, RT, 1h, 2.) ether

3: 83 percent / N,N-diethylaniline / CH₂Cl₂ / 20 h / Ambient temperature

4: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

5: 95 percent / NEt₃ / CH₂Cl₂ / 0.25 h / 0 °C

6: 81 percent / KOtBu / tetrahydrofuran / 0.17 h / 0 °C

7: 86 percent / 10percent aq. HCl / methanol / 0.25 h / Ambient temperature

8: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) RT, 2h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; N,N-diethylaniline; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone;

DOI:10.1248/cpb.38.2712

upstream raw materials:

benzyl bromide

(2R,3S,4R)-N-(tert-butoxycarbonyl)-3,4-dihydroxy-2-<(methoxymethoxy)methyl>pyrrolidine

(2Z,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-penten-5-olide

(2RS,4S)-4-<(tert-butoxycarbonyl)amino>-2-phenylseleno-5-pentanolide

Downstream raw materials:

(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-hydroxymethylpyrrolidine

(2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-4-hydroxybutanyl>-3,4-bis(benzyloxy)pyrrolidine

(S)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-benzyloxy-butan-1-ol

(2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-3-butenyl>-3,4-bis(benzyloxy)pyrrolidine

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