Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

Base Information

Chemical Name:Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester
CAS No.:850559-83-0
Molecular Formula:C₂₈H₃₀N₂O₁₀
Molecular Weight:554.554
Hs Code.:

Synonyms:Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

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Chemical Property of Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

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Technology Process of Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

There total 5 articles about Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl 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: 88.0%

: 850559-82-9
{(1S,2R)-2,3-Dihydroxy-1-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl}-carbamic acid benzyl ester

: 98-88-4
benzoyl chloride

: 850559-83-0
Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

Guidance literature:: With pyridine; In dichloromethane; at -25 ℃; for 2h;
DOI:10.1002/anie.200462298

Reference yield:

: 654644-18-5
5-((2-methoxy)ethoxymethoxy)-2-nitrobenzaldehyde

: 850559-83-0
Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 94 percent / tetrahydrofuran / 6 h / 0 °C

2.1: 79 percent / NaOH; t-butyl hypochlorite; (DHQ)2PHAL / potassium osmate dihydrate / propan-1-ol; H₂O / 2 h / 0 °C

3.1: 70 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

4.1: 88 percent / pyridine / CH₂Cl₂ / 2 h / -25 °C

With pyridine; sodium hydroxide; lithium borohydride; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite; sodium hydride; potassium osmate(VI); In tetrahydrofuran; propan-1-ol; dichloromethane; water; 2.1: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462298

Reference yield:

: 654644-19-6
(E)-3-[5-(2-Methoxy-ethoxymethoxy)-2-nitro-phenyl]-acrylic acid ethyl ester

: 850559-83-0
Benzoic acid (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-3-[5-(2-methoxy-ethoxymethoxy)-2-nitro-phenyl]-propyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 79 percent / NaOH; t-butyl hypochlorite; (DHQ)2PHAL / potassium osmate dihydrate / propan-1-ol; H₂O / 2 h / 0 °C

2: 70 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

3: 88 percent / pyridine / CH₂Cl₂ / 2 h / -25 °C

With pyridine; sodium hydroxide; lithium borohydride; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite; potassium osmate(VI); In tetrahydrofuran; propan-1-ol; dichloromethane; water; 1: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462298