4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

Base Information

Chemical Name:4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol
CAS No.:330476-84-1
Molecular Formula:C₃₁H₃₈O₆
Molecular Weight:506.639
Hs Code.:

Synonyms:4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

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Chemical Property of 4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

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Technology Process of 4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

There total 5 articles about 4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol 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: 13.0%

: 78-84-2
isobutyraldehyde

: 330476-82-9
phenyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl sulfoxide

: 330476-84-1
4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

Guidance literature:: phenyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl sulfoxide; With methyllithium lithium bromide; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.0833333h;

isobutyraldehyde; at -78 ℃; for 0.0833333h; Further stages.;
DOI:10.1021/jo0014515

Reference yield:

: 168985-20-4
3,4,6-Tri-O-benzyl-β-D-glucopyranosyl 2-pyridyl sulfone

: 330476-84-1
4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / Et₃N, DMAP / CH₂Cl₂ / 4 °C

2: 1.) SmI₂, 2.) Bu₄NF / 1.) THF, 20 deg C, 10 min, 2.) THF, 0 deg C, 5 min

With dmap; samarium diiodide; tetrabutyl ammonium fluoride; triethylamine; In dichloromethane;
DOI:10.1002/(sici)1521-3765(19980416)4:4<655::aid-chem655>3.3.co;2-w

Reference yield:

: 127299-77-8,130781-28-1,138181-68-7,130781-27-0
Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 330476-84-1
4,8-anhydro-6,7,9-tri-O-benzyl-1,2-dideoxy-2-C-methyl-D-erythro-L-talo/L-galacto-nonitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 5 h / -78 °C

2.1: MeLi*LiBr; t-BuLi / diethyl ether; tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 13 percent / 0.08 h / -78 °C

With methyllithium lithium bromide; tert.-butyl lithium; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo0014515