(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester
• CAS No.: 870137-17-0
• Molecular Formula: C₂₉H₃₃NO₇
• Molecular Weight: 507.584

Synonyms:(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Chemical Property of (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

There total 4 articles about (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl 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: 60.0%

(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid (1013210-17-7) + benzyl bromide (100-39-0) → (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-17-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃;

DOI:10.1021/ja710363p

Reference yield:

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester (821006-10-4) → (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. HCl

2: aq.LiOH

3: DBU

With hydrogenchloride; lithium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1021/ol052287g

Reference yield:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester (821006-11-5) → (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester (870137-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: aq.LiOH

2: DBU

With lithium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1021/ol052287g

upstream raw materials:

(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid

benzyl bromide

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

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

(2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(3-{(R)-1-[(S)-((S)-2-Amino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-propoxy}-4-hydroxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid

(2S,3R)-3-(4-Benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-prop-2-ynyloxy}-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid benzyl ester

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