(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

Base Information

Chemical Name:(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester
CAS No.:472979-11-6
Molecular Formula:C₁₆H₂₃NO₆
Molecular Weight:325.362
Hs Code.:

Synonyms:(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

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Chemical Property of (2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

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Technology Process of (2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

There total 5 articles about (2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-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: 71.0%

: 5680-80-8
methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

: 472979-05-8
(3R)-4-benzyloxy-3-methoxy-butanic acid

: 472979-11-6
(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

Guidance literature:: With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -25 - 20 ℃;
DOI:10.1021/ol026468j

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 472979-11-6
(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Ti(i-PrO)4; 4 Angstroem molecular sieves; (R)-BINOL / CH₂Cl₂ / -20 °C

2.1: 94 percent / NaH / tetrahydrofuran / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 86 percent / PPh₃ / CH₂Cl₂ / 20 °C

4.1: 98 percent / NaClO₂; KH₂PO₄; H₂O₂ / acetonitrile; methanol; H₂O / 10 °C

5.1: 71 percent / isobutyl chloroformate; N-methylmorpholine / tetrahydrofuran / -25 - 20 °C

With 4-methyl-morpholine; titanium(IV) isopropylate; sodium chlorite; potassium dihydrogenphosphate; 4 A molecular sieve; dihydrogen peroxide; (R)-1,1'-Bi-2-naphthol; sodium hydride; ozone; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ol026468j

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 472979-11-6
(2S,3'R)-2-(4'-benzyloxy-3'-methoxy-butyrylamino)-3-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / NaH / tetrahydrofuran / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 86 percent / PPh₃ / CH₂Cl₂ / 20 °C

3.1: 98 percent / NaClO₂; KH₂PO₄; H₂O₂ / acetonitrile; methanol; H₂O / 10 °C

4.1: 71 percent / isobutyl chloroformate; N-methylmorpholine / tetrahydrofuran / -25 - 20 °C

With 4-methyl-morpholine; sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide; sodium hydride; ozone; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ol026468j