(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol
CAS No.:110104-41-1
Molecular Formula:C₁₇H₂₂O₆S
Molecular Weight:354.424
Hs Code.:

Synonyms:(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

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Chemical Property of (1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

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Technology Process of (1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

There total 1 articles about (1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol 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%

: 6167-32-4
1,6:3,4-dianhydro-2-O-tosyl-D-galactose

: 5674-01-1
2-methylallylmagnesium chloride

: 110104-41-1
(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at 0 ℃; for 24h;
DOI:10.1248/cpb.38.2435

Reference yield:

: 110104-41-1
(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

: 163040-87-7
2-{(2S,3S,4S,5S,6S)-4-Benzyloxy-5-((2S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl)-6-benzyloxymethyl-2-[10-(4-methoxy-benzyloxy)-decyl]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 17 steps

1: NaH, imidazole / tetrahydrofuran / 0.5 h / 0 °C

2: NaN₃, n-tetrabutylammonium iodide / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 72 h / 120 °C

3: 1.) NaH, imidazole, 2.) n-tetrabutylammonium iodide / 1.) THF, DMF, 0 deg C, 2.) r.t., 4 h

4: H₂ / Lindlar catalyst / ethanol / 24 h / 760 Torr / Ambient temperature

5: 1.) pyridine, 2.) Ac₂O / 1.) 90 deg C, 1 h, 2.) 90 deg C, 2 h

6: 87 percent / BF₃*Et₂O / 0.08 h / Ambient temperature

7: 85 percent / TMSOTf / acetonitrile / 8 h / -20 °C

8: 85 percent / DBU / methanol / 10 h

9: 78 percent / NaHMDS / dimethylformamide; toluene / 0.5 h / -60 °C

10: 1.) O₃, 2.) Ph₃P / 1.) MeOH, CH₂Cl₂, -78 deg C, 10 min, 2.) r.t., 45 min

11: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 5 min

12: 95 percent / H₂ / (PPh₃)3RhCl / 24 h / 760 Torr / Ambient temperature

13: 1.) HMDS, n-BuLi / 1.) THF, hexane, 0 deg C, 20 min; toluene, -78 deg C, 30 min, 2.) toluene, 10 min

14: TBAF, 48percent aq. THF / tetrahydrofuran / 24 h / Ambient temperature

15: 10percent BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 5 min, 2.) 0 deg C, 15 min

16: triphenyltin hydride, AIBN / toluene / 0.25 h / 150 °C

17: Swern oxidation

With tetrahydrofuran; pyridine; 1H-imidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; triphenylstannane; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; Lindlar's catalyst; Wilkinson's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00112a040

Reference yield:

: 110104-41-1
(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

: 1027603-80-0
Acetic acid (2S,3R,4S,5S,6S)-6-acetoxymethyl-4-benzyloxy-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(2-methyl-allyl)-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaH, imidazole / tetrahydrofuran / 0.5 h / 0 °C

2: NaN₃, n-tetrabutylammonium iodide / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 72 h / 120 °C

3: 1.) NaH, imidazole, 2.) n-tetrabutylammonium iodide / 1.) THF, DMF, 0 deg C, 2.) r.t., 4 h

4: H₂ / Lindlar catalyst / ethanol / 24 h / 760 Torr / Ambient temperature

5: 1.) pyridine, 2.) Ac₂O / 1.) 90 deg C, 1 h, 2.) 90 deg C, 2 h

6: 87 percent / BF₃*Et₂O / 0.08 h / Ambient temperature

With pyridine; 1H-imidazole; sodium azide; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Lindlar's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; 2-methoxy-ethanol; water;
DOI:10.1021/jo00112a040