(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

Base Information

Chemical Name:(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol
CAS No.:102716-60-9
Molecular Formula:C₁₈H₂₅ClO₄
Molecular Weight:340.847
Hs Code.:

Synonyms:(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

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Chemical Property of (E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

Chemical Property:

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Technology Process of (E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

There total 11 articles about (E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-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:

: 102716-58-5,102716-59-6,115405-15-7,115405-16-8
(E)-3-[(2S,5R)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

: 102716-61-0
(E)-3-[(2S,5R,6R)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

: 102716-60-9
(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h; de 91percent;
DOI:10.1016/S0040-4039(00)98902-0

Reference yield:

: 93662-86-3
isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

: 102716-60-9
(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 24 h

3: imidazole / dimethylformamide / Ambient temperature

4: 1.) sodium hydride / 1.) THF, 2.) THF, DMF, 6.5 h

5: n-Bu₄NF / tetrahydrofuran; acetonitrile

6: 1.) dimethylsulfoxide, oxalyl chloride 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

7: CH₂Cl₂ / -20 - 20 °C

8: 79 percent / (+/-)-10-camphorsulfonic acid / 50 °C

9: diisobutylaluminum hydride / toluene / 1 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)86915-5

Reference yield:

: 115352-42-6
2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside

: 102716-60-9
(E)-3-[(2S,5R,6S)-5-Benzyloxy-6-(2-chloro-ethoxy)-tetrahydro-pyran-2-yl]-2-methyl-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 24 h

2: imidazole / dimethylformamide / Ambient temperature

3: 1.) sodium hydride / 1.) THF, 2.) THF, DMF, 6.5 h

4: n-Bu₄NF / tetrahydrofuran; acetonitrile

5: 1.) dimethylsulfoxide, oxalyl chloride 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

6: CH₂Cl₂ / -20 - 20 °C

7: 79 percent / (+/-)-10-camphorsulfonic acid / 50 °C

8: diisobutylaluminum hydride / toluene / 1 h / -78 °C

With 1H-imidazole; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)86915-5