(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

Base Information

Chemical Name:(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol
CAS No.:108817-28-3
Molecular Formula:C₃₄H₃₃NO₅
Molecular Weight:535.64
Hs Code.:

Synonyms:(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

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Chemical Property of (2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

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Technology Process of (2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

There total 6 articles about (2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol 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: 50.0%

: 108817-25-0
(2S,3R,4S)-2,4-dimethyl-1-O-tritylhex-5-ene-1,3-diol

: 62-23-7
4-nitro-benzoic acid

: 108817-28-3
(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 22 ℃; for 120h;
DOI:10.1021/jo00226a011

Reference yield:

: 88424-95-7
2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol

: 108817-28-3
(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / DMAP / pyridine / 48 h / Ambient temperature

2: trifluoroacetic acid / methanol; H₂O / 48 h / Ambient temperature

3: 70 percent / NaOCH₃ / methanol / 0.5 h / 22 °C

4: 80 percent / CuCN / diethyl ether / 15 h / Ambient temperature

5: 87 percent / DMAP / pyridine / 5 h / 22 °C

6: 50 percent / triphenylphosphine,diethyl azodicarboxylate / tetrahydrofuran / 120 h / 22 °C

With dmap; sodium methylate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; diethyl ether; water;
DOI:10.1021/jo00226a011

Reference yield:

: 108817-22-7
(2R,3R,4S)-epoxy-4-methylhex-5-en-1-ol

: 108817-28-3
(2S,3S,4S)-2,4-dimethyl-3-O-(p-nitrobenzoyl)-1-O-tritylhex-5-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / CuCN / diethyl ether / 15 h / Ambient temperature

2: 87 percent / DMAP / pyridine / 5 h / 22 °C

3: 50 percent / triphenylphosphine,diethyl azodicarboxylate / tetrahydrofuran / 120 h / 22 °C

With dmap; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; diethyl ether;
DOI:10.1021/jo00226a011