(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

Base Information

Chemical Name:(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione
CAS No.:133909-09-8
Molecular Formula:C₂₂H₂₂N₂O₈
Molecular Weight:442.425
Hs Code.:

Synonyms:(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

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Chemical Property of (2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

Chemical Property:

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

There total 7 articles about (2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-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: 94.0%

: 133909-08-7
(2R,3S,4R,5S)-2-benzyloxymethyl-8-(4-methoxybenzyl)-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

: 133909-09-8
(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.333333h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96122-8

Reference yield:

: 129744-34-9,133909-01-0,133909-02-1,133909-03-2,133909-04-3
5-<(2R,3R)-4-benzyloxy-2,3-epoxy-1-t-butyldimethylsilyloxy>butyl-3-(4-methoxybenzyl)hydantoin

: 133909-09-8
(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

Guidance literature:: Multi-step reaction with 4 steps

1: Li(NTMS)2 / tetrahydrofuran / 10 h / Ambient temperature

2: 1.) t-BuOK / 1.) THF, 0 degC 20 min., 2.) 40 min, r.t.

3: 96 percent / OsO₄, N-methylmorpholin-N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 120 h / Ambient temperature

4: 94 percent / Ceric ammonium nitrate / acetonitrile; H₂O / 0.33 h / Ambient temperature

With osmium(VIII) oxide; ammonium cerium(IV) nitrate; potassium tert-butylate; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)96122-8

Reference yield:

: 129829-32-9
5-Z-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin

: 133909-09-8
(2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione

Guidance literature:: Multi-step reaction with 4 steps

1: p-TsOH*H₂O , MS 4A / 2 h / 70 °C / diff. solv.; diff. reac.time; further substrate

2: 1.) t-BuOK / 1.) THF, 0 degC 20 min., 2.) 40 min, r.t.

3: 96 percent / OsO₄, N-methylmorpholin-N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 120 h / Ambient temperature

4: 94 percent / Ceric ammonium nitrate / acetonitrile; H₂O / 0.33 h / Ambient temperature

With osmium(VIII) oxide; ammonium cerium(IV) nitrate; potassium tert-butylate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)96122-8