1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

Base Information

Chemical Name:1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol
CAS No.:131444-84-3
Molecular Formula:C₄₇H₆₂O₁₂
Molecular Weight:819.002
Hs Code.:

Synonyms:1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

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Chemical Property of 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

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Technology Process of 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

There total 9 articles about 1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol 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: 81.0%

: 131456-52-5
(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

: 131444-84-3
1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

Guidance literature:: With pyridine; In toluene; 1) -45 deg C, 1 h, 2) 0 deg C, 30 min;
DOI:10.1021/jo00041a017

Reference yield: 81.0%

: 131456-52-5
(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

: 131444-84-3
1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

Guidance literature:: In pyridine; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)97952-8

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 131444-84-3
1,3-dideoxy-4,5:7,8-di-O-isopropylidene-2-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yl)-6-O-pivaloyl-D-manno-oct-1-enitol

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 15 h / 20 °C

2: 98 percent / pyridine, DMAP / 32 h / Ambient temperature

3: 1) 9-BBN, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 2 h, 2) THF, H₂O, 0 deg C

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

5: 78 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 81 percent / pyridine / toluene / 1) -45 deg C, 1 h, 2) 0 deg C, 30 min

With pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo00041a017