(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

Base Information

Chemical Name:(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane
CAS No.:289667-12-5
Molecular Formula:C₂₉H₄₀O₇Si
Molecular Weight:528.718
Hs Code.:

Synonyms:(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

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Chemical Property of (1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

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Technology Process of (1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

There total 24 articles about (1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane 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:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 289667-12-5
(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: Multi-step reaction with 14 steps

1.1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2.1: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

4.1: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

5.1: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

7.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

8.1: NaH / tetrahydrofuran / 0 - 20 °C

8.2: 95 percent / tetrahydrofuran / 0 - 20 °C

9.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

10.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

11.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C

11.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C

12.1: Li; NH₃ liq. / tetrahydrofuran / 0.33 h / -78 °C

12.2: 74 percent / DDQ / benzene / 3.5 h

13.1: O₃ / methanol / 0.25 h / -78 °C

13.2: Me₂S / methanol / 5 h

14.1: 58.0 mg / pyridine / 16 h

With pyridine; dmap; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; ammonia; water; phosphorus pentoxide; lithium; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 6.1: Swern oxidation / 11.2: Wittig reaction;
DOI:10.1021/jo060803q

Reference yield:

: 289666-91-7
(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

: 289667-12-5
(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: Multi-step reaction with 8 steps

1.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

2.1: NaH / tetrahydrofuran / 0 - 20 °C

2.2: 95 percent / tetrahydrofuran / 0 - 20 °C

3.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

4.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

5.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C

5.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C

6.1: Li; NH₃ liq. / tetrahydrofuran / 0.33 h / -78 °C

6.2: 74 percent / DDQ / benzene / 3.5 h

7.1: O₃ / methanol / 0.25 h / -78 °C

7.2: Me₂S / methanol / 5 h

8.1: 58.0 mg / pyridine / 16 h

With pyridine; n-butyllithium; pyridine-SO₃ complex; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 5.2: Wittig reaction;
DOI:10.1021/jo060803q

Reference yield:

: 289666-90-6
(+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol

: 289667-12-5
(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

2.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 0 - 20 °C

3.2: 95 percent / tetrahydrofuran / 0 - 20 °C

4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

5.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C

6.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C

7.1: Li; NH₃ liq. / tetrahydrofuran / 0.33 h / -78 °C

7.2: 74 percent / DDQ / benzene / 3.5 h

8.1: O₃ / methanol / 0.25 h / -78 °C

8.2: Me₂S / methanol / 5 h

9.1: 58.0 mg / pyridine / 16 h

With pyridine; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 1.1: Swern oxidation / 6.2: Wittig reaction;
DOI:10.1021/jo060803q