(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

Base Information

Chemical Name:(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone
CAS No.:188854-32-2
Molecular Formula:C₂₈H₃₃NO₇
Molecular Weight:495.573
Hs Code.:

Synonyms:(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

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Chemical Property of (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

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Technology Process of (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

There total 4 articles about (2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone 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%

: 189456-77-7
(S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid

: 188854-32-2
(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 24h; Ambient temperature;
DOI:10.1016/S0957-4166(97)00067-0

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 188854-32-2
(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, ether, -80 deg C, 20 min, 2.) THF, ether, from -80 to -20 deg C, 20 h

2: 96 percent / aq. NaOH / dioxane / 5 h / 20 - 60 °C

3: 94 percent / BOP, DIEA / CH₂Cl₂ / 24 h / Ambient temperature

With sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,4-dioxane; dichloromethane;
DOI:10.1016/S0957-4166(97)00067-0

Reference yield:

: 94226-55-8
(dibenzylamino)acetic acid methyl ester

: 188854-32-2
(2S),(3'R)-3'-N-dibenzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-spiropropiolactone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, ether, -80 deg C, 20 min, 2.) THF, ether, from -80 to -20 deg C, 20 h

2: 96 percent / aq. NaOH / dioxane / 5 h / 20 - 60 °C

3: 94 percent / BOP, DIEA / CH₂Cl₂ / 24 h / Ambient temperature

With sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,4-dioxane; dichloromethane;
DOI:10.1016/S0957-4166(97)00067-0