(2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester
• CAS No.: 145929-85-7
• Molecular Formula: C₃₂H₄₀ClN₃O₆Si
• Molecular Weight: 626.225

Synonyms:(2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester

Chemical Property of (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester

There total 11 articles about (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl 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:

isovanillin (621-59-0) → (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester (145929-85-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / CuO, K₂CO₃, pyridine / 12 h / Heating

2: 80 percent / Cl₂, SnCl₄ / CH₂Cl₂ / Ambient temperature

3: NaBH₄ / ethanol / 0 °C

4: imidazole / dimethylformamide / Ambient temperature

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: MnO₂ / benzene / Heating

7: 83 percent / diethyl ether / -78 - 0 °C

8: NaN₃ / dimethylformamide / Ambient temperature

9: 240 h / Ambient temperature; pH 4

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; chlorine; tin(IV) chloride; potassium carbonate; copper(II) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39920001693

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester (145929-85-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / CuO, K₂CO₃, pyridine / 12 h / Heating

2: 80 percent / Cl₂, SnCl₄ / CH₂Cl₂ / Ambient temperature

3: NaBH₄ / ethanol / 0 °C

4: imidazole / dimethylformamide / Ambient temperature

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: MnO₂ / benzene / Heating

7: 83 percent / diethyl ether / -78 - 0 °C

8: NaN₃ / dimethylformamide / Ambient temperature

9: 240 h / Ambient temperature; pH 4

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; chlorine; tin(IV) chloride; potassium carbonate; copper(II) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39920001693

Reference yield:

methyl 4-(5'-formyl-2'-methoxyphenoxy)benzoate (101110-74-1) → (2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid methyl ester (145929-85-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / Cl₂, SnCl₄ / CH₂Cl₂ / Ambient temperature

2: NaBH₄ / ethanol / 0 °C

3: imidazole / dimethylformamide / Ambient temperature

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: MnO₂ / benzene / Heating

6: 83 percent / diethyl ether / -78 - 0 °C

7: NaN₃ / dimethylformamide / Ambient temperature

8: 240 h / Ambient temperature; pH 4

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; chlorine; tin(IV) chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39920001693

upstream raw materials:

methanol

(4S,5R)-3-((2R,3R)-2-Azido-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one

isovanillin

4-methoxycarbonylphenyl bromide

Downstream raw materials:

((2R,3R)-2-tert-Butoxycarbonylamino-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionylamino)-acetic acid benzyl ester

(2R,3R)-2-tert-Butoxycarbonylamino-3-{3-chloro-4-[5-(di-tert-butyl-phenyl-silanyloxymethyl)-2-methoxy-phenoxy]-phenyl}-3-hydroxy-propionic acid

{(2R,3R)-2-tert-Butoxycarbonylamino-3-[3-chloro-4-(5-hydroxymethyl-2-methoxy-phenoxy)-phenyl]-3-hydroxy-propionylamino}-acetic acid

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