(3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide

Base Information

• Chemical Name: (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide
• CAS No.: 138379-99-4
• Molecular Formula: C₁₄H₁₉N₃O₆
• Molecular Weight: 325.321

Synonyms:(3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide

Chemical Property of (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide

Chemical Property:

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Technology Process of (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide

There total 3 articles about (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide 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: 81.0%

(3aR,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4-ureido-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid amide (138379-98-3) → (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide (138379-99-4)

Guidance literature:

With Dowex 50W; In methanol; water; for 72h; Ambient temperature;

DOI:10.1271/bbb.60.1198

Reference yield:

1-Amino-1-carbamoyl-1-dehydro-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose (138457-70-2) → (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide (138379-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / Et₃N / tetrahydrofuran / 1 h / 50 °C

2: 89 percent / ceric ammonium nitrate / methanol; acetonitrile; H₂O / 0.33 h / Ambient temperature

3: 81 percent / Dowex 50W / methanol; H₂O / 72 h / Ambient temperature

With ammonium cerium(IV) nitrate; Dowex 50W; triethylamine; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1271/bbb.60.1198

Reference yield:

(3aR,6R,6aR)-6-Benzyloxymethyl-4-[3-(4-methoxy-benzyl)-ureido]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid amide (179559-93-4) → (3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-ureido-tetrahydro-furan-2-carboxylic acid amide (138379-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / ceric ammonium nitrate / methanol; acetonitrile; H₂O / 0.33 h / Ambient temperature

2: 81 percent / Dowex 50W / methanol; H₂O / 72 h / Ambient temperature

With ammonium cerium(IV) nitrate; Dowex 50W; In methanol; water; acetonitrile;

DOI:10.1271/bbb.60.1198

upstream raw materials:

(3aR,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4-ureido-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid amide

1-Amino-1-carbamoyl-1-dehydro-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

(3aR,6R,6aR)-6-Benzyloxymethyl-4-[3-(4-methoxy-benzyl)-ureido]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid amide

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