[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

Base Information

Chemical Name:[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran
CAS No.:610302-77-7
Molecular Formula:C₁₇H₂₆O₅S
Molecular Weight:342.456
Hs Code.:

Synonyms:[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

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Chemical Property of [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

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Technology Process of [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

There total 8 articles about [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran 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: 84.0%

: 98-59-9
p-toluenesulfonyl chloride

: 610302-75-5
[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-hydroxyethyl)tetrahydropyran

: 610302-77-7
[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 15h;

Reference yield:

: 85593-49-3
1,6-anhydro-2,3,4-trideoxy-2,4-di-C-methyl-β-D-ribo-hexopyranoside

: 610302-77-7
[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 43 percent / Dowex 50W (H(+)) / 7.5 h / 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: (i-PrO)3TiCl / tetrahydrofuran; diethyl ether

3.2: 690.6 mg / tetrahydrofuran; diethyl ether / 12 h / 0 °C

4.1: 84 percent / DMAP / pyridine / 15 h / 20 °C

With triisopropoxytitanium(IV) chloride; dmap; oxalyl dichloride; Dowex 50W (H(+)); dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

Reference yield:

: 128790-96-5
Methanesulfonic acid (1S,2R,3S,4R,5R)-2-methyl-4-phenylsulfanylmethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

: 610302-77-7
[2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / Na; liq. NH₃ / tetrahydrofuran / 1 h / -78 °C

2.1: 43 percent / Dowex 50W (H(+)) / 7.5 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: (i-PrO)3TiCl / tetrahydrofuran; diethyl ether

4.2: 690.6 mg / tetrahydrofuran; diethyl ether / 12 h / 0 °C

5.1: 84 percent / DMAP / pyridine / 15 h / 20 °C

With triisopropoxytitanium(IV) chloride; dmap; oxalyl dichloride; Dowex 50W (H(+)); ammonia; sodium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;