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

Base Information

• Chemical Name: (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester
• CAS No.: 188245-72-9
• Molecular Formula: C₃₄H₃₆N₂O₁₁
• Molecular Weight: 648.667

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

Chemical Property of (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

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Technology Process of (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester

There total 3 articles about (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-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: 90.0%

(S)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester (188245-68-3) → (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester (188245-72-9)

Guidance literature:

With acetic acid; In water; at 80 ℃; for 2h;

DOI:10.1016/S0040-4039(96)02490-2

Reference yield:

N-Fmoc serine phenacyl ester (125760-26-1) → (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester (188245-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / BF₃*Et₂O / tetrahydrofuran / -20 °C

2: 90 percent / 80percent CH₃COOH / H₂O / 2 h / 80 °C

With boron trifluoride diethyl etherate; acetic acid; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(96)02490-2

Reference yield:

N-((2S,4aR,6S,7R,8R,8aR)-6,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (172139-01-4) → (S)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 2-oxo-2-phenyl-ethyl ester (188245-72-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / DBU / CH₂Cl₂ / -20 °C

2: 68 percent / BF₃*Et₂O / tetrahydrofuran / -20 °C

3: 90 percent / 80percent CH₃COOH / H₂O / 2 h / 80 °C

With boron trifluoride diethyl etherate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4039(96)02490-2

upstream raw materials:

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

N-Fmoc serine phenacyl ester

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

Downstream raw materials:

(S)-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)-propionic acid 2-oxo-2-phenyl-ethyl ester

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