(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Base Information

Chemical Name:(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester
CAS No.:132183-21-2
Molecular Formula:C₄₆H₄₂N₄O₁₀
Molecular Weight:810.86
Hs Code.:

(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Synonyms:(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

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Chemical Property of (S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

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Technology Process of (S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

There total 8 articles about (S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl 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: 67.0%

: 125760-26-1
N-Fmoc serine phenacyl ester

: 132183-19-8
(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 132183-21-2
(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane;
DOI:10.1016/S0040-4039(00)97201-0

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 132183-21-2
(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / acetonitrile

2: 85 percent / NaH / tetrahydrofuran / Heating

3: 97 percent / n-Bu₄NF, AcOH / tetrahydrofuran

4: 78 percent / DAST / tetrahydrofuran

5: 67 percent / Cp₂HfCl₂, AgClO₄ / CH₂Cl₂

With bis(cyclopentadienyl)hafnium dichloride; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)97201-0

Reference yield:

: 132183-13-2
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate

: 132183-21-2
(S)-3-((2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / imidazole / dimethylformamide / 2.5 h / 60 °C

2: NaOMe / methanol

3: p-TsOH / acetonitrile

4: 85 percent / NaH / tetrahydrofuran / Heating

5: 97 percent / n-Bu₄NF, AcOH / tetrahydrofuran

6: 78 percent / DAST / tetrahydrofuran

7: 67 percent / Cp₂HfCl₂, AgClO₄ / CH₂Cl₂

With 1H-imidazole; bis(cyclopentadienyl)hafnium dichloride; tetrabutyl ammonium fluoride; sodium methylate; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)97201-0