(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Base Information

Chemical Name:(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester
CAS No.:188245-75-2
Molecular Formula:C₃₈H₄₂N₂O₁₁
Molecular Weight:702.758
Hs Code.:

(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

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Chemical Property of (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

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Technology Process of (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

There total 4 articles about (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric 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: 58.0%

: 77-76-9
2,2-dimethoxy-propane

: 188245-73-0
(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

: 188245-75-2
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(96)02490-2

Reference yield:

: 125760-27-2
N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester

: 188245-75-2
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 32 percent / BF₃*Et₂O / tetrahydrofuran / -20 °C

2: 91 percent / 80percent CH₃COOH / H₂O / 2 h / 80 °C

3: 58 percent / TsOH / dimethylformamide

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(96)02490-2

Reference yield:

: 172139-01-4
N-((2S,4aR,6S,7R,8R,8aR)-6,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

: 188245-75-2
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / DBU / CH₂Cl₂ / -20 °C

2: 32 percent / BF₃*Et₂O / tetrahydrofuran / -20 °C

3: 91 percent / 80percent CH₃COOH / H₂O / 2 h / 80 °C

4: 58 percent / TsOH / dimethylformamide

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(96)02490-2