(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

Base Information

Chemical Name:(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene
CAS No.:214060-16-9
Molecular Formula:C₂₄H₃₄O₃Si
Molecular Weight:398.618
Hs Code.:

Synonyms:(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

Chemical Property:

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Technology Process of (3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

There total 5 articles about (3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene 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:

: 127665-68-3
(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

: 214060-16-9
(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

2: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; In 2,2,4-trimethylpentane; dichloromethane;
DOI:10.1248/cpb.47.308

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 214060-16-9
(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / benzene / 17 h / Ambient temperature

2: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

3: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

4: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; diisobutylaluminium hydride; In 2,2,4-trimethylpentane; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.47.308

Reference yield:

: 95514-04-8,129029-85-2,120346-83-0
(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 214060-16-9
(3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / 2 h / -78 - -55 °C

2: 98 percent / benzene / 17 h / Ambient temperature

3: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

4: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

5: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In 2,2,4-trimethylpentane; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.47.308