(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

Base Information

Chemical Name:(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol
CAS No.:1448445-88-2
Molecular Formula:C₂₃H₃₂O₃Si
Molecular Weight:384.591
Hs Code.:

Synonyms:(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

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Chemical Property of (3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

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Technology Process of (3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

There total 7 articles about (3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol 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: 70.0%

: 303044-42-0
(2R,3R)-2-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}-3-ethenyloxirane

: 1448445-88-2
(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

Guidance literature:: With water; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; at 20 ℃; for 2.5h;
DOI:10.1002/hlca.201200164

Reference yield:

: 303044-40-8
(2E,5R)-5-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hex-2-en-1-ol

: 1448445-88-2
(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 8 h / -20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

2.2: 0.5 h / -78 - 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / 0 °C

3.2: 0.5 h / 0 °C

4.1: scandium tris(trifluoromethanesulfonate); water / tetrahydrofuran / 2.5 h / 20 °C

With titanium(IV) isopropylate; oxalyl dichloride; water; sodium hexamethyldisilazane; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation / 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1002/hlca.201200164

Reference yield:

: 303044-41-9
(2R,3R)-3-{(2R)-2-{[(1,1-dimethylethyl)diphenylsilyl]oxy}propyl}oxirane-2-methanol

: 1448445-88-2
(3S,4R,6R)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}hept-1-ene-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

1.2: 0.5 h / -78 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / 0 °C

2.2: 0.5 h / 0 °C

3.1: scandium tris(trifluoromethanesulfonate); water / tetrahydrofuran / 2.5 h / 20 °C

With oxalyl dichloride; water; sodium hexamethyldisilazane; dimethyl sulfoxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1002/hlca.201200164