1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

Base Information

Chemical Name:1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose
CAS No.:168103-69-3
Molecular Formula:C₂₁H₂₄O₆
Molecular Weight:372.418
Hs Code.:

Synonyms:

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Chemical Property of 1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

Chemical Property:

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Technology Process of 1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

There total 2 articles about 1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose 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:

: (1R,2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(isopropoxy-dimethyl-silanyl)-methyl]-6,8-dioxa-bicyclo[3.2.1]octan-2-ol

: 168103-69-3
1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

Guidance literature:: With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; for 12h; Yield given; Heating;
DOI:10.1021/jo00114a028

Reference yield:

: 122588-50-5
(dimethylisopropoxysilyl)methylmagnesium chloride

: 138709-45-2
1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose

: 168103-69-3
1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

Guidance literature:: With dihydrogen peroxide; sodium hydrogencarbonate; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min; -78 deg C to -15 deg C 2 h, 2.) THF, MeOH, reflux, 12 h;
DOI:10.1021/jo961534e

Reference yield:

: 168103-69-3
1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

: 185155-22-0
(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarbaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / imidazole / dimethylformamide / Ambient temperature

2: Ac₂O / 1.5 h / 68 °C

3: MeONa / methanol / 2 h / Ambient temperature

4: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

5: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

6: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

7: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

8: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

9: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

10: TBAF / tetrahydrofuran / 1 h / 0 °C

11: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; dipyridinium dichromate; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; acetic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo961534e