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

Base Information

Chemical Name:2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol
CAS No.:153153-30-1
Molecular Formula:C₃₀H₃₂O₆
Molecular Weight:488.58
Hs Code.:

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

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

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

There total 7 articles about 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-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: 92.0%

: 108-24-7
acetic anhydride

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

: 153153-30-1
2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/j.carres.2005.01.008

Reference yield: 80.0%

: 108-24-7
acetic anhydride

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

: 153153-30-1
2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

Guidance literature:: (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde; With sodium tetrahydroborate; ethanol; for 0.333333h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1002/ejoc.201801004

Reference yield:

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

: 153153-30-1
2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / NaBH₄ / methanol / 16 h / 20 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
DOI:10.1016/j.carres.2005.01.008