(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Base Information

• Chemical Name: (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester
• CAS No.: 821006-85-3
• Molecular Formula: C₂₈H₂₉NO₈
• Molecular Weight: 507.54

Synonyms:(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Chemical Property of (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Chemical Property:

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Technology Process of (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

There total 1 articles about (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic 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: 93.0%

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester (821006-11-5) + benzyl chloroformate (501-53-1,94274-21-2) → (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (821006-85-3)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/jo048854f

Reference yield: 91.0%

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (821006-85-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-(tert-butyldimethylsilanyloxy)propionic acid methyl ester (821006-12-6)

Guidance literature:

With pyridine; silver nitrate; at 20 ℃; for 17h;

DOI:10.1021/jo048854f

Reference yield: 87.0%

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (821006-85-3) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-(tert-butyldimethylsilanyloxy)propionic acid methyl ester (821006-12-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja710363p

upstream raw materials:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester

benzyl chloroformate

Downstream raw materials:

(2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(benzyloxycarbonylmethylamino)-3-(tert-butyldimethylsilanyloxy)propionic acid methyl ester

(2S,3R)-2-(Benzyloxycarbonyl-methyl-amino)-3-(4-benzyloxy-3-hydroxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

2-(benzyloxycarbonylmethylamino)-3-[4-benzyloxy-3-(1-ethyl-1-methylallyloxy)phenyl]-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester

2-(benzyloxycarbonylmethylamino)-3-[4-benzyloxy-3-(3-methylpent-2-enyloxycarbonyloxy)phenyl]-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester

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