(2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol

Base Information

• Chemical Name: (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol
• CAS No.: 167084-00-6
• Molecular Formula: C₃₁H₄₄N₄O₇S
• Molecular Weight: 616.779

Synonyms:(2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol

Chemical Property of (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol

There total 6 articles about (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol 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: 82.0%

2-azido-1,3-O-benzylidene-D-ribo-1,3,4-octadecanetriol (117168-58-8) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol (167084-00-6)

Guidance literature:

With pyridine; In toluene; at 60 ℃; for 24h;

DOI:10.1016/S0957-4166(00)86295-3

Reference yield:

1,3-O-benzylidene-(D-arabino/L-xylo)-1,2,3,4-octadecanetetrol (303752-90-1) → (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol (167084-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / PDC / dimethylformamide / 72 h / Ambient temperature

2: 1.) CH₃CHO, SmI₂, 2.) NaOMe / 1.) THF, -10 deg C, 2 h, 2.) CH₂Cl₂, CH₃OH, 12 h

3: 75 percent / pyridine / -30 °C

4: 63 percent / NaN₃ / dimethylformamide / 90 °C

5: 82 percent / pyridine / toluene / 24 h / 60 °C

With pyridine; dipyridinium dichromate; sodium azide; samarium diiodide; sodium methylate; acetaldehyde; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0957-4166(00)86295-3

Reference yield:

(2R,3S)-1,3-O-benzylidene-1,2,3-octadecanetriol-4-one (150162-78-0) → (2S,3S,4R)-2-azido-1,3-O-benzylidene-4-(4-nitrobenzenesulfonyl)-1,3-octadecanediol (167084-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CH₃CHO, SmI₂, 2.) NaOMe / 1.) THF, -10 deg C, 2 h, 2.) CH₂Cl₂, CH₃OH, 12 h

2: 75 percent / pyridine / -30 °C

3: 63 percent / NaN₃ / dimethylformamide / 90 °C

4: 82 percent / pyridine / toluene / 24 h / 60 °C

With pyridine; sodium azide; samarium diiodide; sodium methylate; acetaldehyde; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0957-4166(00)86295-3

upstream raw materials:

2-azido-1,3-O-benzylidene-D-ribo-1,3,4-octadecanetriol

4-Nitrobenzenesulfonyl chloride

(2R,4S,4aS,6S,8aR)-2-((2S,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-ol

(2R,3R,4R)-1,3-O-benzylidene-1,2,3,4-octadecanetetrol

Downstream raw materials:

(2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol

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