(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol
CAS No.:871590-07-7
Molecular Formula:C₃₄H₃₄O₆
Molecular Weight:538.64
Hs Code.:

Synonyms:(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

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Chemical Property of (2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

There total 1 articles about (2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-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: 80.0%

: 93-03-8
(3,4-dimethoxyphenyl)methanol

: 474459-57-9
4-O-mesyl-6-O-trityl-D-glucal

: 871590-07-7
(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With potassium tert-butylate; In benzene; at 23 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield: 99.0%

: 871590-07-7
(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 871590-08-8
tert-butyl-[6-(3,4-dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-yloxy]-dimethyl-silane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

: 871590-07-7
(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

: 871590-28-2
{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]-propoxy}-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 21 steps

1.1: 99 percent / imidazole / dimethylformamide / 2 h / 23 °C

2.1: 80 percent / DDQ / CH₂Cl₂ / 0.5 h / 23 °C / pH 7

3.1: 93 percent / TEMPO; Bu₄NCl; NCS / CH₂Cl₂ / 2 h / 23 °C / pH 8.6

4.1: 98 percent / diethyl ether / 2 h / -40 °C

5.1: 98 percent / NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.1: 86 percent / BCl₃ / CH₂Cl₂ / 2 h / -20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / -20 °C

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

9.1: CSA / CH₂Cl₂ / 7 h / 23 °C

10.1: 98 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

11.1: 100 percent / tetrahydrofuran / 0.5 h / -20 °C

12.1: 89 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

13.1: 67 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 23 °C

14.1: 98 percent / DIBALH / CH₂Cl₂ / 1 h / -78 °C

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

16.1: tetrahydrofuran / 2 h / -78 °C

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

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

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

19.1: 100 percent / t-BuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 23 °C

20.1: 99 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / 15 h / -78 °C

21.1: 96 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; N-chloro-succinimide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hexamethyldisilazane; boron trichloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 15.1: Swern oxidation / 16.1: Brown's asymmetric crotylboration / 16.2: Brown's asymmetric crotylboration;
DOI:10.1016/j.tetlet.2005.09.163