(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

Base Information

Chemical Name:(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole
CAS No.:1580541-85-0
Molecular Formula:C₂₀H₂₃NO₆S₂
Molecular Weight:437.538
Hs Code.:

Synonyms:(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

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Chemical Property of (2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

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Technology Process of (2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

There total 5 articles about (2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole 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%

: 1580541-71-4
(E)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-enylthio}-1,3-benzothiazole

: 1580541-85-0
(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

Guidance literature:: With methanesulfonamide; AD-mix β; In water; tert-butyl alcohol; at 0 ℃; for 12h; enantioselective reaction;
DOI:10.1002/ejoc.201301269

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 1580541-85-0
(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 10 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 1 h / 0 °C

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - 0 °C

4.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 10 h / 0 - 20 °C

5.1: AD-mix β; methanesulfonamide / tert-butyl alcohol; water / 12 h / 0 °C

With methanesulfonamide; AD-mix β; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; mineral oil; tert-butyl alcohol; 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/ejoc.201301269

Reference yield:

: 13709-07-4
2,5-bis(methoxymethoxy)benzaldehyde

: 1580541-85-0
(2'S,3'R)-2-{3'-[2'',5''-bis(methoxymethoxy)phenyl]-2',3'-dihydroxyprop-2-enylthio}-1,3-benzothiazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 1 h / 0 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - 0 °C

3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 10 h / 0 - 20 °C

4.1: AD-mix β; methanesulfonamide / tert-butyl alcohol; water / 12 h / 0 °C

With methanesulfonamide; AD-mix β; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol; 1.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/ejoc.201301269