3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 528841-71-6
• Molecular Formula: C₃₂H₃₀N₂O₆
• Molecular Weight: 538.6

Synonyms:3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

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Technology Process of 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 2 articles about 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 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: 48.0%

N-3-benzoylthymine (4330-20-5) + (1R,2R,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexan-2-ol (528841-65-8) → 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (528841-71-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -45 - 20 ℃; for 16.5h;

DOI:10.1016/S0040-4020(02)01528-4

Reference yield:

(1R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-2-en-1-ol (259659-53-5) → 3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (528841-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 48 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 16.5 h / -45 - 20 °C

With 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)01528-4

Reference yield: 80.0%

3-Benzoyl-1-((1R,2S,4S,5S)-4-benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (528841-71-6) → (5aS,7S,8S,8aS)-7-Benzyloxy-8-benzyloxymethyl-8-hydroxy-3-methyl-6,7,8,8a-tetrahydro-5aH-cyclopenta[4,5]oxazolo[3,2-a]pyrimidin-2-one (528841-73-8)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(02)01528-4

upstream raw materials:

N-3-benzoylthymine

(1R,2R,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexan-2-ol

(1R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-2-en-1-ol

Downstream raw materials:

(5aS,7S,8S,8aS)-7-Benzyloxy-8-benzyloxymethyl-8-hydroxy-3-methyl-6,7,8,8a-tetrahydro-5aH-cyclopenta[4,5]oxazolo[3,2-a]pyrimidin-2-one

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