6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Base Information

Chemical Name:6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
CAS No.:729596-19-4
Molecular Formula:C₁₈H₂₅NO₈
Molecular Weight:383.398
Hs Code.:

Synonyms:6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

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Chemical Property of 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

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Technology Process of 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

There total 14 articles about 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-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: 88.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 108788-52-9
6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

: 729596-19-4
6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Guidance literature:: 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose; With palladium 10% on activated carbon; ammonium formate; In methanol; for 1h; Reflux; Inert atmosphere;

benzyl chloroformate; With sodium hydrogencarbonate; In methanol; water; at 0 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tetasy.2010.01.007

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 729596-28-5
(1R,2R)-2-Amino-1-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propane-1,3-diol

: 729596-19-4
6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Guidance literature:: With sodium hydrogencarbonate; In methanol; water; at 0 - 25 ℃; for 3.5h;
DOI:10.1021/jo049509t

Reference yield:

: 108788-49-4
ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 729596-19-4
6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

Guidance literature:: Multi-step reaction with 6 steps

1.1: K₃Fe(CN)6; K₂CO₃; (DHQD)2PHAL / potassium osmate; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

3.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

3.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

4.1: LiAlH₄ / tetrahydrofuran / 3 h / 0 - 25 °C

5.1: ammonium formate / Pd/C / methanol / 1 h / Heating

6.1: 0.47 g / NaHCO₃ / methanol; H₂O / 3.5 h / 0 - 25 °C

With pyridine; lithium aluminium tetrahydride; thionyl chloride; sodium azide; ammonium formate; sodium hydrogencarbonate; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); palladium on activated charcoal; methanesulfonamide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo049509t