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

Base Information

Chemical Name:((2S,4R,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester
CAS No.:866823-62-3
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

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

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

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

There total 9 articles about ((2S,4R,6R)-4-Benzyloxy-6-hydroxymethyl-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: 82.0%

: 866823-58-7
ethyl 5-benzyloxy-7,8-dihydroxy-(E,5R,7R)-2-octenoate

: ((2R,4R,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

: 866823-62-3
((2S,4R,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

: 866823-59-8
(2R,4S)-5-hexene-1,2,4-triol

: 866823-62-3
((2S,4R,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 76 percent / p-toluenesulfonic acid / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 8 h / Heating

3.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

3.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

4.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

5.1: 89 percent / benzene / 12 h / 20 °C

6.1: 91 percent / camphor-10-sulfonic acid / methanol / 12 h / 20 °C

7.1: 82 percent / NaH / tetrahydrofuran / 4 h / -78 °C

With dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dimethyl sulfoxide; benzene; 5.1: Wittig olefination / 7.1: intramolecular oxy-anione Michael addition;
DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

: 117064-89-8
1-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(2S)-3-buten-2-ol

: 866823-62-3
((2S,4R,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 96 percent / tetrahydrofuran / 8 h / Heating

2.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

2.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

3.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

4.1: 89 percent / benzene / 12 h / 20 °C

5.1: 91 percent / camphor-10-sulfonic acid / methanol / 12 h / 20 °C

6.1: 82 percent / NaH / tetrahydrofuran / 4 h / -78 °C

With dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dimethyl sulfoxide; benzene; 4.1: Wittig olefination / 6.1: intramolecular oxy-anione Michael addition;
DOI:10.1016/j.tetasy.2005.07.001