α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester

Base Information

• Chemical Name: α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester
• CAS No.: 854443-29-1
• Molecular Formula: C₂₅H₃₃N₃O₆
• Molecular Weight: 471.554

Synonyms:α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester

Chemical Property of α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester

There total 8 articles about α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl 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:

N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5) → α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester (854443-29-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: isobutyl chloroformate; N-methyl morpholine / CH₂Cl₂ / 0.25 h / -15 °C

1.2: 92 percent / CH₂Cl₂ / 2 h / -15 - 20 °C

2.1: 94 percent / diethyl ether; tetrahydrofuran / -78 °C

3.1: 0.47 g / K-selectride / tetrahydrofuran / 19 h / -78 °C

4.1: 84 percent / aq. KOH / ethanol / 6 h / Heating

5.1: 85 percent / triflyl azide; 4-dimethylaminopyridine; CuSO₄ / CH₂Cl₂ / 2 h / 20 °C

6.1: tetrabutylammonium hydrogensulfate; aq. NaOH / benzene / 1.5 h / 20 °C

7.1: 0.832 g / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 2.5 h / 20 °C

With 4-methyl-morpholine; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone; benzene; 2.1: Grignard reaction;

DOI:10.1016/j.tet.2005.03.061

Reference yield:

{(S)-1-[(S)-1-Azido-2-(4-benzyloxy-phenyl)-ethyl]-but-3-enyloxy}-acetic acid tert-butyl ester → α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester (854443-29-1)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2005.03.061

Reference yield:

(S)-N-methoxy-N-methyl-2-benzyloxycarbonylamino-3-(4-benzyloxyphenyl)-propanoic amide (854443-23-5) → α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester (854443-29-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / diethyl ether; tetrahydrofuran / -78 °C

2: 0.47 g / K-selectride / tetrahydrofuran / 19 h / -78 °C

3: 84 percent / aq. KOH / ethanol / 6 h / Heating

4: 85 percent / triflyl azide; 4-dimethylaminopyridine; CuSO₄ / CH₂Cl₂ / 2 h / 20 °C

5: tetrabutylammonium hydrogensulfate; aq. NaOH / benzene / 1.5 h / 20 °C

6: 0.832 g / osmium tetroxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 2.5 h / 20 °C

With dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone; benzene; 1: Grignard reaction;

DOI:10.1016/j.tet.2005.03.061

upstream raw materials:

(2S,3S)-2-amino-1-(4-benzyloxyphenyl)-hex-5-en-3-ol

(2S,3S)-2-azido-1-(4-benzyloxyphenyl)-hex-5-en-3-ol

(4S,5S)-5-allyl-4-(4-benzyloxybenzyl)-oxazolidin-2-one

(S)-N-methoxy-N-methyl-2-benzyloxycarbonylamino-3-(4-benzyloxyphenyl)-propanoic amide

Downstream raw materials:

C₇₅H₉₃N₇O₁₁Si

[(1S,2S)-1-(2-{(S)-4-Allyloxycarbonylamino-1-[(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine-1-carbonyl]-butylamino}-ethyl)-2-azido-3-(4-benzyloxy-phenyl)-propoxy]-acetic acid tert-butyl ester

[(1S,2S)-2-azido-3-(4-benzyloxyphenyl)-1-(2-oxoethyl)-prop-1-oxy]-acetic acid tert-butyl ester

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