3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Base Information

Chemical Name:3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose
CAS No.:729596-25-2
Molecular Formula:C₂₄H₃₁NO₁₁
Molecular Weight:509.51
Hs Code.:

Synonyms:3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

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Chemical Property of 3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

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Technology Process of 3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

There total 8 articles about 3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose 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: 79.0%

: 108-24-7
acetic anhydride

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

: 729596-25-2
3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: With pyridine; at 20 ℃; for 8h;
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

: 729596-25-2
3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 7 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

7.1: 79 percent / pyridine / 8 h / 20 °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

Reference yield:

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

: 729596-25-2
3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 3 steps

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

2: 0.47 g / NaHCO₃ / methanol; H₂O / 3.5 h / 0 - 25 °C

3: 79 percent / pyridine / 8 h / 20 °C

With pyridine; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; water;
DOI:10.1021/jo049509t