((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Base Information

Chemical Name:((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester
CAS No.:202526-20-3
Molecular Formula:C₁₈H₂₆O₅
Molecular Weight:322.401
Hs Code.:

Synonyms:((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

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Chemical Property of ((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

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Technology Process of ((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

There total 10 articles about ((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 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: 90.0%

: 202526-19-0
[(3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

: 202526-20-3
((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -10 - 20 ℃;
DOI:10.1021/jo971863m

Reference yield:

: 202526-15-6
(2R,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butane-1,3-diol

: 202526-20-3
((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

2: 85 percent / NaH / dimethylformamide / 25 °C

3: 94 percent / TBAF / tetrahydrofuran / 25 °C

4: Swern / -78 °C

5: 1 N HCl / tetrahydrofuran / 25 °C

6: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

7: 93 percent / PCC / CH₂Cl₂ / 25 °C

8: 92 percent / LiHMDS / tetrahydrofuran / -78 °C

9: 90 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / -10 - 20 °C

With hydrogenchloride; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo971863m

Reference yield:

: 202526-32-7
(2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-butan-2-ol

: 202526-20-3
((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / NaH / dimethylformamide / 25 °C

2: 94 percent / TBAF / tetrahydrofuran / 25 °C

3: Swern / -78 °C

4: 1 N HCl / tetrahydrofuran / 25 °C

5: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

6: 93 percent / PCC / CH₂Cl₂ / 25 °C

7: 92 percent / LiHMDS / tetrahydrofuran / -78 °C

8: 90 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / -10 - 20 °C

With hydrogenchloride; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo971863m