Phenol, 4-[(2S,4R,6S)-4-bromotetrahydro-6-[2-[4-(phenylmethoxy)phenyl]ethyl]- 2H-pyran-2-yl]-, 4-methylbenzenesulfonate

Base Information

Chemical Name:Phenol, 4-[(2S,4R,6S)-4-bromotetrahydro-6-[2-[4-(phenylmethoxy)phenyl]ethyl]- 2H-pyran-2-yl]-, 4-methylbenzenesulfonate
CAS No.:477284-02-9
Molecular Formula:C33H33BrO5S
Molecular Weight:621.592
Hs Code.:
Mol file:477284-02-9.mol

Synonyms:

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Chemical Property of Phenol, 4-[(2S,4R,6S)-4-bromotetrahydro-6-[2-[4-(phenylmethoxy)phenyl]ethyl]- 2H-pyran-2-yl]-, 4-methylbenzenesulfonate

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Technology Process of Phenol, 4-[(2S,4R,6S)-4-bromotetrahydro-6-[2-[4-(phenylmethoxy)phenyl]ethyl]- 2H-pyran-2-yl]-, 4-methylbenzenesulfonate

There total 6 articles about Phenol, 4-[(2S,4R,6S)-4-bromotetrahydro-6-[2-[4-(phenylmethoxy)phenyl]ethyl]- 2H-pyran-2-yl]-, 4-methylbenzenesulfonate 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%

: 477284-01-8
Acetic acid 3-(4-benzyloxy-phenyl)-1-{(S)-1-[4-(toluene-4-sulfonyloxy)-phenyl]-but-3-enyloxy}-propyl ester

: 477284-02-9
Toluene-4-sulfonic acid 4-{(2S,4R,6S)-6-[2-(4-benzyloxy-phenyl)-ethyl]-4-bromo-tetrahydro-pyran-2-yl}-phenyl ester

Guidance literature:: With stannic bromide; In dichloromethane; at -78 ℃; for 1.3h;
DOI:10.1021/ol026751i

Reference yield:

: 50463-48-4
3-(4-benzyloxyphenyl)propanoic acid

: 477284-02-9
Toluene-4-sulfonic acid 4-{(2S,4R,6S)-6-[2-(4-benzyloxy-phenyl)-ethyl]-4-bromo-tetrahydro-pyran-2-yl}-phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / DCC / DMAP / CH₂Cl₂ / 12 h / 20 °C

2: DIBAL-H / -78 °C

3: DMAP; pyridine; DIBAL-H / CH₂Cl₂; hexane / -78 - 0 °C

4: 84 percent / SnBr₄ / CH₂Cl₂ / 1.3 h / -78 °C

With pyridine; dmap; stannic bromide; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; dmap; In hexane; dichloromethane; 4: Prins cyclization;
DOI:10.1021/ol026751i

Reference yield:

: 80459-48-9
4-tosyloxybenzaldehyde

: 477284-02-9
Toluene-4-sulfonic acid 4-{(2S,4R,6S)-6-[2-(4-benzyloxy-phenyl)-ethyl]-4-bromo-tetrahydro-pyran-2-yl}-phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: (S)-BINOL; Ti(O-iPr)4

2: 94 percent / DCC / DMAP / CH₂Cl₂ / 12 h / 20 °C

3: DIBAL-H / -78 °C

4: DMAP; pyridine; DIBAL-H / CH₂Cl₂; hexane / -78 - 0 °C

5: 84 percent / SnBr₄ / CH₂Cl₂ / 1.3 h / -78 °C

With pyridine; titanium(IV) isopropylate; dmap; (S)-[1,1']-binaphthalenyl-2,2'-diol; stannic bromide; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; dmap; In hexane; dichloromethane; 1: Keck's allylation / 5: Prins cyclization;
DOI:10.1021/ol026751i