(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

Base Information

Chemical Name:(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine
CAS No.:1053651-03-8
Molecular Formula:C₃₀H₃₃NO₅
Molecular Weight:487.596
Hs Code.:

Synonyms:(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

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Chemical Property of (S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

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Technology Process of (S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

There total 7 articles about (S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine 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:

: 161147-37-1
Methyl 6-azido-2,3,4-tri-O-benzyl-6,7,8-trideoxy-L-glycero-α-D-gluco-oct-7-ynopyranoside

: 1053651-03-8
(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

Guidance literature:: With 1.3-propanedithiol; triethylamine; In methanol; at 45 ℃; for 24h;
DOI:10.1021/jo00108a030

Reference yield:

: 83051-88-1
methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 1053651-03-8
(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi, MgBr₂ / 1.) hexane, Et₂O, -5 deg C, 30 min, 2.) -30 deg C to r.t.

2: 74 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

3: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

4: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

With 1.3-propanedithiol; n-butyllithium; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; magnesium bromide; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00108a030

Reference yield:

: 103597-22-4
methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside

: 1053651-03-8
(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / Ambient temperature

2: 93 percent / K₂CO₃ / methanol / 0.33 h / Ambient temperature

3: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

4: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

With 1.3-propanedithiol; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00108a030