1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Base Information

Chemical Name:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol
CAS No.:153547-53-6
Molecular Formula:C₂₈H₃₀O₅
Molecular Weight:446.543
Hs Code.:

Synonyms:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

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Chemical Property of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

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Technology Process of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

There total 3 articles about 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-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: 90.0%

: 136883-91-5
(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde

: 153547-53-6
1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 153547-53-6
1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 2 steps

1: 2.90 g / POCl₃ / 8 h / 20 °C

2: 90 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; trichlorophosphate; In methanol; 1: Vilsmeier-Haack reaction;

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 153547-53-6
1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 2 steps

1: trichlorophosphate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 0.25 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; trichlorophosphate; In methanol; N,N-dimethyl-formamide; 1: |Vilsmeier-Haack Formylation;
DOI:10.1021/jo401613v