5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

Base Information

Chemical Name:5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone
CAS No.:140193-69-7
Molecular Formula:C₂₈H₃₃NO₈
Molecular Weight:511.572
Hs Code.:

Synonyms:5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

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Chemical Property of 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

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Technology Process of 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

There total 6 articles about 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone 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: 84.0%

: Benzyl-[((2R,3S,4R)-3,4-dihydroxy-5-oxo-tetrahydro-furan-2-yl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamic acid benzyl ester

: 77-76-9
2,2-dimethoxy-propane

: 140193-69-7
5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

Guidance literature:: With toluene-4-sulfonic acid; for 5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)88132-1

Reference yield:

: 131319-74-9
(R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine

: 140193-69-7
5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

Guidance literature:: Multi-step reaction with 4 steps

1: 66 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / -85 °C

2: 68 percent / 7percent aq. NaHCO₃ / dioxane / 3 h / Ambient temperature

3: 59 percent / KMnO₄ / dicyclohexano-18-crown-6-ether / CH₂Cl₂ / 4 h / Ambient temperature

4: 84 percent / p-TsOH / 5 h / Ambient temperature

With potassium permanganate; boron trifluoride diethyl etherate; sodium hydrogencarbonate; toluene-4-sulfonic acid; perhydrodibenzo-18-crown-6; In 1,4-dioxane; dichloromethane;
DOI:10.1016/S0040-4020(01)88132-1

Reference yield:

: 140193-75-5,140193-76-6
5-[Benzylamino-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5H-furan-2-one

: 140193-69-7
5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / 7percent aq. NaHCO₃ / dioxane / 3 h / Ambient temperature

2: 59 percent / KMnO₄ / dicyclohexano-18-crown-6-ether / CH₂Cl₂ / 4 h / Ambient temperature

3: 84 percent / p-TsOH / 5 h / Ambient temperature

With potassium permanganate; sodium hydrogencarbonate; toluene-4-sulfonic acid; perhydrodibenzo-18-crown-6; In 1,4-dioxane; dichloromethane;
DOI:10.1016/S0040-4020(01)88132-1