[5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione

Base Information

• Chemical Name: [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione
• CAS No.: 129744-45-2
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356

Synonyms:[5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione

Chemical Property of [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione

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Technology Process of [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione

There total 21 articles about [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-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: 100.0%

[5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxa-2-thioxo-spiro[4.4]nonan-4-one (145121-83-1) → [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (129744-45-2)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In water; acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1016/S0008-6215(01)00239-7

Reference yield: 99.0%

methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate (339540-30-6) → [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (129744-45-2)

Guidance literature:

With ammonia; In methanol; at 37 ℃; for 4h;

DOI:10.1016/S0008-6215(02)00217-3

Reference yield: 25.0%

1-Amino-1-carbamoyl-1-dehydro-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose (138457-70-2) + 1,1'-carbonyldiimidazole (530-62-1) → [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (129744-45-2) + [5R-(5α,7β,8α,9α)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione (133908-91-5)

Guidance literature:

In benzene; at 70 ℃; for 5.5h;

DOI:10.1016/S0040-4020(01)96124-1

upstream raw materials:

tributylphosphine

carbon dioxide

1-β-Azido-1-dehydro-1-α-carbamoyl-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

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

Downstream raw materials:

[5R-(5α,7β,8α,9α)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione

<2R,3R,4R,5S>-6-N-Acetyl-2-benzyloxymethyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4.4>nonane-7,9-dione

<2R,3S,4R,5S>-2-Benzyloxymethyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4.4>nonane-7,9-dione

[5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione

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