Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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Chemical Name:Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester
CAS No.:339588-02-2
Molecular Formula:C₄₃H₄₃ClN₂O₁₄
Molecular Weight:847.272
Hs Code.:

Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Synonyms:Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

There total 10 articles about Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl 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: 97.0%

: 339588-01-1
{4-[(2R,3S,4R,5R,6S)-4-Benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-2-ylmethoxymethyl]-2-nitro-phenoxy}-acetic acid tert-butyl ester

: 541-88-8
Chloroacetic anhydride

: 339588-02-2
Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja003856c

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 339588-02-2
Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃ / acetonitrile / 1 h / 60 °C

2: 97 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; potassium carbonate; In dichloromethane; acetonitrile;
DOI:10.1021/ja003856c

Reference yield:

: 3011-34-5
4-hydroxy-3-nitrobenzaldehyde

: 339588-02-2
Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-(4-tert-butoxycarbonylmethoxy-3-nitro-benzyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / K₂CO₃ / acetonitrile / 60 °C

2.1: CaSO₄ / methanol / 2 h

2.2: CSA / methanol / 0.5 h / 40 °C

3.1: CaSO₄ / acetonitrile / 2 h

3.2: 95 percent / CSA / acetonitrile / 2 h / 55 °C

4.1: 93 percent / NaH / dimethylformamide / 4 h / 0 °C

5.1: 100 percent / HCl; NaBH₃CN / dioxane; tetrahydrofuran / 3 h / 20 °C / pH 1 - 2

6.1: 92 percent / Pd(PPh₃)4; Et₃SiH; AcOH / toluene / 1 h / 20 °C

7.1: 92 percent / K₂CO₃ / acetonitrile / 1 h / 60 °C

8.1: 97 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; triethylsilane; calcium sulfate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium cyanoborohydride; potassium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja003856c