3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester

Base Information

• Chemical Name: 3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester
• CAS No.: 868368-00-7
• Molecular Formula: C₂₇H₃₇N₃O₈
• Molecular Weight: 531.606

Synonyms:3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester

Chemical Property of 3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester

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Technology Process of 3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester

There total 1 articles about 3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid 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: 85.0%

Boc-Taa-OEt + Benzyloxymethyl chloride (3587-60-8) → 3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester (868368-00-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.07.089

Reference yield:

3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester (868368-00-7) → Boc-[Taa(BOM)]-OH

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tet.2005.07.089

Reference yield:

3-[5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl]-propionic acid ethyl ester (868368-00-7) → Boc-[Taa(BOM)]2-OEt (868368-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiOH*H₂O / dioxane; H₂O / 3 h / 0 - 20 °C

2.1: N-methylmorpholine; 1-hydroxybenzotriazole monohydrate; [N,N,N',N'-tetramethyl-O-(benzotriazol-1-yl)uronium][BF₄] / acetonitrile / 0.5 h / 20 °C

2.2: 75 percent / N-methylmorpholine / acetonitrile / 12 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-hydroxybenzotriazol-hydrate; In 1,4-dioxane; water; acetonitrile;

DOI:10.1016/j.tet.2005.07.089

upstream raw materials:

Benzyloxymethyl chloride

Downstream raw materials:

Boc-[Taa(BOM)]2-OEt

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