2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 239446-22-1
• Molecular Formula: C₂₄H₂₇NO₉
• Molecular Weight: 473.48

Synonyms:2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

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Technology Process of 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 2 articles about 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 40.0%

2-Bromo-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (239446-17-4) → 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (239446-22-1)

Guidance literature:

With 3,5-dihydroxyphenol; sodium nitrite; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(99)00935-1

Reference yield:

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) → 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (239446-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / CH₂Cl₂ / -5 deg C -> r.t., 2 h

2: 40 percent / NaNO₂; phloroglucinol / dimethylformamide / 2 h / 20 °C

With pyridine; 3,5-dihydroxyphenol; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Substitution;

DOI:10.1016/S0040-4039(99)00935-1

Reference yield:

4-nitrobenzyl chloride (100-14-1) + 2-Nitro-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (239446-22-1) → (R)-2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester + (S)-2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Irradiation;

DOI:10.1016/S0040-4039(99)00935-1

upstream raw materials:

2-Bromo-propionic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

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