(5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one

Base Information

• Chemical Name: (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one
• CAS No.: 869749-13-3
• Molecular Formula: C₂₄H₂₄N₂O₄
• Molecular Weight: 404.466

Synonyms:(5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one

Chemical Property of (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one

Chemical Property:

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Technology Process of (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one

There total 2 articles about (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one 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: 85.2%

(1'R,2'R,3'R,4'R)-1-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)uracil → (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one (869749-13-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b312276j

Reference yield:

(1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane (873298-16-9) → (5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one (869749-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 53.6 percent / DBU / dimethylformamide / Heating

2: 85.2 percent / DEAD; Ph₃P / tetrahydrofuran / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b312276j

Reference yield: 93.4%

(5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-a]pyrimidine-2-one (869749-13-3) → (1'R,2'S,3'R,4'R)-1-(4-benzyloxy-3-benzyloxymethyl-2-hydroxycyclopentyl)uracil

Guidance literature:

With sodium hydroxide; Heating;

DOI:10.1039/b312276j

upstream raw materials:

(1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane

Downstream raw materials:

(5aR,7R,8S,8aS)-7-benzyloxy-8-benzyloxymethyl-5a,7,8,8a-tetrahydro-2H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

(5aR,7R,8S,8aS)-8-(4,4'-dimethoxytrityloxymethyl)-5a,7,8,8a-tetrahydro-7-hydroxy-1H,6H-cyclopenta[4,5]oxazolo[3,2-c]pyrimidine-2,4(3H)-dione

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