(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Base Information

Chemical Name:(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol
CAS No.:137742-93-9
Molecular Formula:C₃₈H₅₁NO₈Si
Molecular Weight:677.91
Hs Code.:

(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4-<N-(benzyloxycarbonyl)amino>-6-<tert-butyldimethylsilyl)oxy>-2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Synonyms:(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Chemical Property:

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Technology Process of (2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

There total 12 articles about (2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol 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: 85.0%

: 108-24-7
acetic anhydride

: 137768-17-3
(2S,3R,4S,5S)-3-(Allyloxy)-4--6-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-2-<1-(allyloxy)naphth-3-yl>-2-hexanol

: 137742-93-9
(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Guidance literature:: With pyridine; dmap; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jo00028a045

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 137742-93-9
(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / DBU / CH₂Cl₂ / 0.67 h / 0 °C

2: 85 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1021/jo00028a045

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 137742-93-9
(2S,3R,4S,5S)-5-Acetoxy-3-(allyloxy)-4--6--2-<1-(allyloxy)naphth-3-yl>-2-hexanol

Guidance literature:: Multi-step reaction with 6 steps

1: Na₂CO₃ / diethyl ether / 3 h / 5 °C

2: 90 percent / activated MnO₂ / CHCl₃ / 5 h / Heating

3: 88 percent / diethyl ether / 1) -30 deg C, 30 min., 2) 0 deg C, 30 min., 3) r.t., 1 h

4: 90 percent / propane-1,3-dithiol, BF₃*Et₂O / CH₂Cl₂ / 1) -78 deg C, 2 h, 2) -40 deg C, 2 h, 3) 0 deg C, 1 h

5: 75 percent / DBU / CH₂Cl₂ / 0.67 h / 0 °C

6: 85 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 1.3-propanedithiol; dmap; manganese(IV) oxide; boron trifluoride diethyl etherate; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/jo00028a045