(E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

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Chemical Name:(E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone
CAS No.:126394-14-7
Molecular Formula:C₃₂H₄₂O₇
Molecular Weight:538.681
Hs Code.:

Synonyms:(E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

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Chemical Property of (E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

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Technology Process of (E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

There total 42 articles about (E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone 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:

: 109536-51-8,142226-16-2,69940-04-1
1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 126394-14-7
(Z)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

Guidance literature:: Multi-step reaction with 10 steps

1: NaIO₄ / H₂O; methanol / 0 °C

2: NaBH₄ / methanol; H₂O / 1 h

3: 1) NaH / 1) DMSO, RT, 2) DMSO, 60 deg C

4: 64 percent / 4N HCl / tetrahydrofuran / 3.5 h / 55 °C

5: 100 percent / NaIO₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

6: 74 percent / LiAlH₄ / tetrahydrofuran

7: 96 percent / CSA / acetone / 0.5 h

8: 87 percent / hydrogen / Raney-Ni (W-2) / ethanol / 7 h / Ambient temperature

9: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

10: 1) NaH / 1) DMSO, THF, 0 deg C, 2) DMSO, THF, RT

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; Raney-Ni (W-2); In tetrahydrofuran; methanol; ethanol; water; acetone;
DOI:10.1248/cpb.37.1705

Reference yield:

: 109536-51-8,142226-16-2,69940-04-1
1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 126394-14-7
(E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

Guidance literature:: Multi-step reaction with 10 steps

1: NaIO₄ / H₂O; methanol / 0 °C

2: NaBH₄ / methanol; H₂O / 1 h

3: 1) NaH / 1) DMSO, RT, 2) DMSO, 60 deg C

4: 64 percent / 4N HCl / tetrahydrofuran / 3.5 h / 55 °C

5: 100 percent / NaIO₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

6: 74 percent / LiAlH₄ / tetrahydrofuran

7: 96 percent / CSA / acetone / 0.5 h

8: 87 percent / hydrogen / Raney-Ni (W-2) / ethanol / 7 h / Ambient temperature

9: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

10: 1) NaH / 1) DMSO, THF, 0 deg C, 2) DMSO, THF, RT

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; Raney-Ni (W-2); In tetrahydrofuran; methanol; ethanol; water; acetone;
DOI:10.1248/cpb.37.1705

Reference yield:

: 115693-78-2,142226-15-1,69940-02-9
1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 126394-14-7
(E)-1-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3-[(4R,5R)-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxan-4-yl]-propenone

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / MeOH, H₂SO₄ / 54 h / Ambient temperature

2: NaIO₄ / H₂O; methanol / 0 °C

3: NaBH₄ / methanol; H₂O / 1 h

4: 1) NaH / 1) DMSO, RT, 2) DMSO, 60 deg C

5: 64 percent / 4N HCl / tetrahydrofuran / 3.5 h / 55 °C

6: 100 percent / NaIO₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

7: 74 percent / LiAlH₄ / tetrahydrofuran

8: 96 percent / CSA / acetone / 0.5 h

9: 87 percent / hydrogen / Raney-Ni (W-2) / ethanol / 7 h / Ambient temperature

10: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

11: 1) NaH / 1) DMSO, THF, 0 deg C, 2) DMSO, THF, RT

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; Raney-Ni (W-2); In tetrahydrofuran; methanol; ethanol; water; acetone;
DOI:10.1248/cpb.37.1705