6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Base Information

Chemical Name:6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose
CAS No.:131013-17-7
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

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Chemical Property of 6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

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Technology Process of 6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

There total 1 articles about 6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose 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: 100.0%

: 2457-93-4
(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole

: phenylmagnesium chloride

: 131013-17-7
6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; a) 1 h at -50 deg C and 30 min at -30 deg C;
DOI:10.1021/jo00003a040

Reference yield: 95.0%

: 131013-17-7
6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

: 98-59-9
p-toluenesulfonyl chloride

: 131013-18-8
6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: With pyridine; at 45 ℃; for 24h;
DOI:10.1021/jo00003a040

Reference yield:

: 131013-17-7
6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

: 125356-66-3,119463-16-0
(+)-preussin

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / pyridine / 24 h / 45 °C

2: 90 percent / NaN₃ / dimethylsulfoxide / 3 h / 80 °C

3: 84 percent / methanolic HCl / 12 h / Ambient temperature

4: 95 percent / pyridine / CH₂Cl₂ / 1 h at -50 deg C, 30 min at 0 deg C

5: 66 percent / H₂ / palladium black / ethyl acetate / 6 h / 760 Torr

6: 86 percent / pyridine / CH₂Cl₂ / from -78 deg C to r.t. over a period for 1 h

7: 100 percent / aq. formic acid / tetrahydrofuran / 2 h / Heating

8: 1) n-butyllithium, HMPA / 1) THF, hexan, 15 min at -78 deg C and 30 min at 0 deg C, 2) THF, 30 min at -78 deg C and 12 h at r.t.

9: 100 percent / H₂ / 5percent Pd-C / ethanol / 24 h / 760 Torr

10: 100 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; formic acid; sodium azide; hydrogen; palladium on activated charcoal; palladium; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo00003a040