3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Base Information

Chemical Name:3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol
CAS No.:871590-27-1
Molecular Formula:C₃₃H₄₂O₄
Molecular Weight:502.694
Hs Code.:

Synonyms:3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

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Chemical Property of 3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

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Technology Process of 3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

There total 29 articles about 3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-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: 16.0%

: (5S,7R,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-9,10-dimethyl-8-(naphthalen-2-ylmethoxy)-1,6-dioxa-spiro[4.5]decane

: 871590-27-1
3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 5h;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

: 871590-05-5
(3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3,4-dimethyl-tetrahydro-pyran-2-one

: 871590-27-1
3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

2.1: 100 percent / tetrahydrofuran / 0.5 h / -20 °C

3.1: 89 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

4.1: 67 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 23 °C

5.1: 98 percent / DIBALH / CH₂Cl₂ / 1 h / -78 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.17 h / -78 °C

7.1: tetrahydrofuran / 2 h / -78 °C

7.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 12 h / 23 °C

8.1: t-BuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 23 °C

9.1: Bu₄NF / tetrahydrofuran / 20 h / 23 °C

10.1: 100 percent / t-BuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 23 °C

11.1: 99 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / 15 h / -78 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation / 7.1: Brown's asymmetric crotylboration / 7.2: Brown's asymmetric crotylboration;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

: 871590-12-4
(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3,4-dimethyl-tetrahydro-pyran-2-one

: 871590-27-1
3-[(2R,3S,4S,5R,6S)-6-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-3,4-dimethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / -20 °C

2.1: aq. LiOH / tetrahydrofuran / 3 h / 23 °C

3.1: CSA / CH₂Cl₂ / 7 h / 23 °C

4.1: 98 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

5.1: 100 percent / tetrahydrofuran / 0.5 h / -20 °C

6.1: 89 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

7.1: 67 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 23 °C

8.1: 98 percent / DIBALH / CH₂Cl₂ / 1 h / -78 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.17 h / -78 °C

10.1: tetrahydrofuran / 2 h / -78 °C

10.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 12 h / 23 °C

11.1: t-BuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 23 °C

12.1: Bu₄NF / tetrahydrofuran / 20 h / 23 °C

13.1: 100 percent / t-BuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 23 °C

14.1: 99 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / 15 h / -78 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; lithium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 9.1: Swern oxidation / 10.1: Brown's asymmetric crotylboration / 10.2: Brown's asymmetric crotylboration;
DOI:10.1016/j.tetlet.2005.09.163