(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

Base Information

Chemical Name:(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol
CAS No.:404936-45-4
Molecular Formula:C₂₀H₃₂O₆S
Molecular Weight:400.536
Hs Code.:

Synonyms:(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

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Chemical Property of (4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

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Technology Process of (4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

There total 10 articles about (4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol 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: 93.0%

: 124-63-0
methanesulfonyl chloride

: 404936-44-3
(4R,6S)-4,6-O-isopropylidene-9-(benzyloxy)-1,4,6-nonanetriol

: 404936-45-4
(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

Guidance literature:: With diisopropylamine; In dichloromethane; at 20 ℃; for 0.416667h;
DOI:10.1021/ol017261d

Reference yield:

: 4344-84-7,21461-84-7,53558-93-3,83829-70-3
5-oxo-tetrahydro-furan-2-carboxylic acid

: 404936-45-4
(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 70 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating

2.1: 91 percent / (+/-)-camphersulfonic acid / acetone / 3 h / 35 °C

3.1: NaH / tetrahydrofuran / 0.75 h

3.2: 84 percent / tetrahydrofuran / 16 h

4.1: 93 percent / AcOH / 3 h / 20 °C

5.1: CH₃C(OCH₃)3; PPTS / CH₂Cl₂ / 3 h / 20 °C

5.2: AcBr / CH₂Cl₂ / 0.75 h

5.3: 99 percent / K₂CO₃ / methanol / 2 h

6.1: t-BuLi; TMEDA / tetrahydrofuran; pentane / 3 h / -20 °C

6.2: 89 percent / tetrahydrofuran; pentane / 2 h / -20 °C

7.1: 90 percent / Hg(ClO₄)2*4H₂O; iPr₂NH / tetrahydrofuran / 1 h

8.1: (EtO)2BMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

8.2: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 3 h / -78 °C

9.1: 97 percent / (+/-)-camphersulfonic acid / 1 h / 20 °C

10.1: 93 percent / iPr₂NH / CH₂Cl₂ / 0.42 h / 20 °C

With Trimethyl orthoacetate; lithium aluminium tetrahydride; mercury(II) perchlorate; methyldiethoxyborane; N,N,N,N,-tetramethylethylenediamine; 10-camphorsufonic acid; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; pentane;
DOI:10.1021/ol017261d

Reference yield:

: 19131-21-6
(2S)-pentane-1,2,5-triol

: 404936-45-4
(4R,6S)-1-methylsulfonyloxy-4,6-O-isopropylidene-9-(benzyloxy)-4,6-nonanediol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 91 percent / (+/-)-camphersulfonic acid / acetone / 3 h / 35 °C

2.1: NaH / tetrahydrofuran / 0.75 h

2.2: 84 percent / tetrahydrofuran / 16 h

3.1: 93 percent / AcOH / 3 h / 20 °C

4.1: CH₃C(OCH₃)3; PPTS / CH₂Cl₂ / 3 h / 20 °C

4.2: AcBr / CH₂Cl₂ / 0.75 h

4.3: 99 percent / K₂CO₃ / methanol / 2 h

5.1: t-BuLi; TMEDA / tetrahydrofuran; pentane / 3 h / -20 °C

5.2: 89 percent / tetrahydrofuran; pentane / 2 h / -20 °C

6.1: 90 percent / Hg(ClO₄)2*4H₂O; iPr₂NH / tetrahydrofuran / 1 h

7.1: (EtO)2BMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

7.2: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 3 h / -78 °C

8.1: 97 percent / (+/-)-camphersulfonic acid / 1 h / 20 °C

9.1: 93 percent / iPr₂NH / CH₂Cl₂ / 0.42 h / 20 °C

With Trimethyl orthoacetate; mercury(II) perchlorate; methyldiethoxyborane; N,N,N,N,-tetramethylethylenediamine; 10-camphorsufonic acid; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; pentane;
DOI:10.1021/ol017261d