(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

Base Information

Chemical Name:(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester
CAS No.:910484-39-8
Molecular Formula:C₃₂H₄₂O₇S
Molecular Weight:570.747
Hs Code.:

(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

Synonyms:(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

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Chemical Property of (S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

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Technology Process of (S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

There total 6 articles about (S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid 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: 84.0%

: 910484-38-7
(S)-4-[(5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

: 910484-39-8
(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

Guidance literature:: With osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tert-butyl alcohol; at 20 ℃; for 12h;
DOI:10.1021/ol061072j

Reference yield:

: 910484-46-7
(S)-2-Benzyloxy-4-[(5R,6R)-6-formyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester

: 910484-39-8
(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 68 percent / KHMDS; 18-crown-6 / toluene; tetrahydrofuran / 48 h / -78 - 20 °C

2: 84 percent / aq. OsO₄; (DHQ)2PYR; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol / 12 h / 20 °C

With osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); 18-crown-6 ether; potassium hexamethylsilazane; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; toluene; tert-butyl alcohol; 1: Horner-Wadsworth-Emmons reaction / 2: Sharpless dihydroxylation;
DOI:10.1021/ol061072j

Reference yield:

: 910484-37-6
(S)-2-Benzyloxy-4-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester

: 910484-39-8
(S)-4-[(2R,3S,5R,6S)-6-((E)-2-Benzenesulfonyl-propenyl)-2,3-dihydroxy-5-isopropyl-2-methyl-cyclohex-(E)-ylidene]-2-benzyloxy-2-methyl-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

2: 68 percent / KHMDS; 18-crown-6 / toluene; tetrahydrofuran / 48 h / -78 - 20 °C

3: 84 percent / aq. OsO₄; (DHQ)2PYR; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol / 12 h / 20 °C

With osmium(VIII) oxide; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); 18-crown-6 ether; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; 1: Swern oxidation / 2: Horner-Wadsworth-Emmons reaction / 3: Sharpless dihydroxylation;
DOI:10.1021/ol061072j