6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

Base Information

Chemical Name:6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose
CAS No.:84247-11-0
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

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Chemical Property of 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

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Technology Process of 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

There total 18 articles about 6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose 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: 89.0%

: 100-39-0
benzyl bromide

: 78785-27-0
3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

: 84247-11-0
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 48h; Ambient temperature;
DOI:10.1016/0008-6215(82)84027-5

Reference yield:

: 73683-73-5
methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-glucopyranoside

: 84247-11-0
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / DMAP / pyridine / 1.5 h / Ambient temperature

2: 67.3 g / NBS, BaCO₃ / CCl₄ / 23 h / 80 °C

3: LiAlH₄ / tetrahydrofuran / 2 h / 75 °C

4: 22.6 g / conc. H₂SO₄ / 1.5 h / Ambient temperature

5: 11.5 g / NaOH/MeOH / 3 h / Ambient temperature

6: 49 percent / anhydrous FeCl₃ / 5.5 h / Ambient temperature

7: 84 percent / Jones reagent / acetone / 1.5 h / Ambient temperature

8: 94 percent / 55percent NaH, Me₂SO / 1.5 h / Ambient temperature

9: 68 percent / 1.) Me₂S*BH₃; 2.) 3M NaOH, 30percent H₂O₂ / CH₂Cl₂; ethanol / 2.5 h / Ambient temperature

10: 89 percent / 55percent NaH / tetrahydrofuran / 48 h / Ambient temperature

With methanol; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; iron(III) chloride; sodium hydride; dimethyl sulfoxide; barium carbonate; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; acetone;
DOI:10.1016/0008-6215(82)84027-5

Reference yield:

: 53872-67-6
1,2:5,6-di-O-isopropylidene-3-C-methyl-3-deoxy-α-D-glucofuranose

: 84247-11-0
6-O-benzyl-3,5-dideoxy-1,2-O-isopropylidene-3,5-di-C-methyl-β-L-idofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: 90percent aq. AcOH / 1.5 h / 60 °C

2: 85 percent / DMAP / pyridine / 0.42 h / 0 °C

3: 86 percent / Jones reagent / acetone / 1.5 h / Ambient temperature

4: 52 percent / 4M methylsulfinylmethanide anion/Me₂SO / diethyl ether / 0.25 h / Ambient temperature

5: 95 percent / 1M aq. NaOH / methanol / 0.25 h

6: 13 percent / H₂ / (Ph₃P)3RhCl / benzene / 3 h / Ambient temperature

7: 89 percent / 55percent NaH / tetrahydrofuran / 48 h / Ambient temperature

With dmap; sodium hydroxide; jones reagent; dimethyl sulfoxide; deprotonated form; hydrogen; sodium hydride; acetic acid; dimethyl sulfoxide; Wilkinson's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; acetone; benzene;
DOI:10.1016/0008-6215(82)84027-5