(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

Base Information

Chemical Name:(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate
CAS No.:918961-67-8
Molecular Formula:C₃₇H₆₅IO₆Si
Molecular Weight:760.909
Hs Code.:

Synonyms:(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

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Chemical Property of (2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

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Technology Process of (2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

There total 8 articles about (2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate 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: 61.0%

: 918961-66-7
(2R,3S,4S,5S,6S,8R)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoic acid

: 216493-79-7
(E)-(3R,4R)-6-iodo-4-methyl-5-hexen-3-ol

: 918961-67-8
(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

Guidance literature:: (2R,3S,4S,5S,6S,8R)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 3h;

(E)-(3R,4R)-6-iodo-4-methyl-5-hexen-3-ol; With dmap; In benzene; at 20 ℃; for 24h;
DOI:10.1021/jo062047u

Reference yield:

: (2S,4R)-2,4-Dimethyl-5-triisopropylsilanyloxy-pentanal

: 918961-67-8
(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

1.2: 78 percent / CH₂Cl₂ / 2.5 h / -78 - -10 °C

2.1: 88 percent / LiBH₄ / tetrahydrofuran; methanol / 0.75 h / 0 °C

3.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

4.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

5.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

6.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

6.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

7.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

8.1: Et₃N; 2,4,6-trichlorobenzoylchloride / tetrahydrofuran / 3 h / 20 °C

8.2: 61 percent / DMAP / benzene / 24 h / 20 °C

With lithium hydroxide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.2: Evans Aldol Reaction / 5.1: Swern Oxidation / 6.2: Evans Aldol Reaction;
DOI:10.1021/jo062047u

Reference yield:

: 918961-61-2
(2S,3S,4S,6R)-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptane-1,3-diol

: 918961-67-8
(2R,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

2.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

3.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

4.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

4.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

5.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

6.1: Et₃N; 2,4,6-trichlorobenzoylchloride / tetrahydrofuran / 3 h / 20 °C

6.2: 61 percent / DMAP / benzene / 24 h / 20 °C

With lithium hydroxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; toluene; 3.1: Swern Oxidation / 4.2: Evans Aldol Reaction;
DOI:10.1021/jo062047u