Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

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Chemical Name:Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester
CAS No.:653568-49-1
Molecular Formula:C₁₉H₂₃IO₆
Molecular Weight:474.293
Hs Code.:

Synonyms:Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

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Chemical Property of Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

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Technology Process of Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

There total 9 articles about Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl 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: 91.0%

: 653568-39-9
Benzoic acid (R)-methoxycarbonyl-{(2S,5S,6S)-2-methoxy-5,6-dimethyl-4-[1-trimethylsilanyl-meth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-methyl ester

: 653568-49-1
Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

Guidance literature:: With N-iodo-succinimide; In acetonitrile; at 0 ℃; for 3h;
DOI:10.1021/ja038787r

Reference yield:

: 3724-55-8
methyl but-3-enoate

: 653568-49-1
Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 63 percent / CpRu(CH₃CN)3PF₆ / acetone / 3.5 h / 20 °C

2: 100 percent / triethylamine / CH₂Cl₂ / 0.33 h / -78 °C

3: 96 percent / NMO; OsO₄ / acetone; H₂O / 60 h / 2 °C

4: 70 percent / DMAP; Et₃N / CH₂Cl₂ / -78 - -45 °C

5: Dess-Martin periodinane; Na₂CO₃ / CH₂Cl₂ / 0.67 h / 20 °C

6: CSA / methanol / 3 h / 20 °C

7: 103 mg / LHMDS / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.75 h / -70 °C

8: 91 percent / NIS / acetonitrile / 3 h / 0 °C

With dmap; N-iodo-succinimide; osmium(VIII) oxide; N-methyl-2-indolinone; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; camphor-10-sulfonic acid; sodium carbonate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/ja038787r

Reference yield:

: 653568-34-4
(2S,3S)-3-Methyl-5-trimethylsilanyl-pent-4-yn-2-ol

: 653568-49-1
Benzoic acid (R)-{(2S,5S,6S)-4-[1-iodo-meth-(Z)-ylidene]-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl}-methoxycarbonyl-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 63 percent / CpRu(CH₃CN)3PF₆ / acetone / 3.5 h / 20 °C

2: 100 percent / triethylamine / CH₂Cl₂ / 0.33 h / -78 °C

3: 96 percent / NMO; OsO₄ / acetone; H₂O / 60 h / 2 °C

4: 70 percent / DMAP; Et₃N / CH₂Cl₂ / -78 - -45 °C

5: Dess-Martin periodinane; Na₂CO₃ / CH₂Cl₂ / 0.67 h / 20 °C

6: CSA / methanol / 3 h / 20 °C

7: 103 mg / LHMDS / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.75 h / -70 °C

8: 91 percent / NIS / acetonitrile / 3 h / 0 °C

With dmap; N-iodo-succinimide; osmium(VIII) oxide; N-methyl-2-indolinone; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; camphor-10-sulfonic acid; sodium carbonate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/ja038787r