1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

Base Information

Chemical Name:1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose
CAS No.:899431-84-6
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

Synonyms:1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

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Chemical Property of 1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

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Technology Process of 1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

There total 10 articles about 1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose 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:

: 899431-82-4
(2S,3S)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidin-3-ol

: 899431-84-6
1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

Guidance literature:: Multi-step reaction with 2 steps

1: ammonium formate / Pd/C / methanol / 1 h / 80 °C

2: 0.06 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; water;
DOI:10.1021/jo0601617

Reference yield:

: 899431-81-3
(1S,2S)-1-Benzylamino-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-2-ol

: 899431-84-6
1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

Guidance literature:: Multi-step reaction with 3 steps

1.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 3 h / 20 °C

1.2: 73 percent / sodium borohydride / tetrahydrofuran; H₂O

2.1: ammonium formate / Pd/C / methanol / 1 h / 80 °C

3.1: 0.06 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With mercury(II) diacetate; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo0601617

Reference yield:

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

: 899431-84-6
1,2-O-isopropylidene-5,7,8-trideoxy-5,8-(N-benzoxycarbonylamino)-6(S)-hydroxy-α-L-glycero-L-ido-oct-1,4-furanose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2.20 g / sodium metaperiodate / H₂O / 6 h

2.1: tetrahydrofuran / 1 h / -50 °C

2.2: 86 percent / aqueous KOH / methanol / 0.17 h / 90 °C

3.1: 98 percent / aqueous KOH / methanol / 48 h / 90 °C

4.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 3 h / 20 °C

4.2: 73 percent / sodium borohydride / tetrahydrofuran; H₂O

5.1: ammonium formate / Pd/C / methanol / 1 h / 80 °C

6.1: 0.06 g / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With potassium hydroxide; sodium periodate; mercury(II) diacetate; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; 2.1: Grignard reaction;
DOI:10.1021/jo0601617