(2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane

Base Information

• Chemical Name: (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane
• CAS No.: 189456-92-6
• Molecular Formula: C₂₉H₄₂N₂O₇
• Molecular Weight: 530.662
• Mol file: 189456-92-6.mol

Synonyms:(2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane

Chemical Property of (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane

There total 18 articles about (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane 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: 48.0%

(2S,5S,3E)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene (189456-83-5) → (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane (189456-92-6) + (2S,3R,4R,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; tert-butyl alcohol; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(97)00160-9

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane (189456-92-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 86 percent / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 81 percent / LiBH₄ / tetrahydrofuran / 3 h / 20 °C

3.1: 85 percent / sulfur trioxide pyridine complex; Et₃N / dimethylsulfoxide / 1 h / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: MeOH; DIBAL-H / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

6.1: 0.94 g / Na₂HPO₄; Na-Hg / methanol / 12 h / 0 - 20 °C

7.1: 65 percent / sodium / liquid ammonia; tetrahydrofuran / 1 h / -33 °C

8.1: 48 percent / N-methylmorpholine oxide / OsO₄ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

With pyridine; disodium hydrogenphosphate; lithium borohydride; n-butyllithium; sodium amalgam; sodium; sulfur trioxide pyridine complex; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; ammonia; water; dimethyl sulfoxide; tert-butyl alcohol; 1.1: alkoxycarbonylation / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation / 6.1: Elimination / 7.1: debenzylation / 8.1: dihydroxylation;

DOI:10.1016/S0040-4020(97)00160-9

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (2S,3S,4S,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-dihydroxyhexane (189456-92-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaBH₄; I₂ / tetrahydrofuran / 18 h / Heating

2.1: 95 percent / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 90 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 83 percent / methanol; tetrahydrofuran / 3 h / 20 °C

5.1: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

6.2: MeOH; DIBAL-H / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

8.1: 0.94 g / Na₂HPO₄; Na-Hg / methanol / 12 h / 0 - 20 °C

9.1: 65 percent / sodium / liquid ammonia; tetrahydrofuran / 1 h / -33 °C

10.1: 48 percent / N-methylmorpholine oxide / OsO₄ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

With pyridine; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; iodine; sodium; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; ammonia; water; tert-butyl alcohol; 1.1: Reduction / 2.1: alkoxycarbonylation / 3.1: Tosylation / 4.1: Substitution / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Acetylation / 8.1: Elimination / 9.1: debenzylation / 10.1: dihydroxylation;

DOI:10.1016/S0040-4020(97)00160-9

upstream raw materials:

(2S,5S,3E)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene

L-phenylalanine

di-tert-butyl dicarbonate

L-Phenylalaninol