(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

Base Information

Chemical Name:(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol
CAS No.:346701-76-6
Molecular Formula:C₂₈H₄₅BrO₅Si
Molecular Weight:569.652
Hs Code.:

(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

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Chemical Property of (3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

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Technology Process of (3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

There total 12 articles about (3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol 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:

: 171004-48-1
5-bromo-5-hexen-2-yn-1-ol

: 346701-76-6
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: Red-Al / diethyl ether

2: (+)-diisopropyl L-(+)-tartrate; TBHP; 4 Angstroem MS / Ti(Oi-Pr)4 / CH₂Cl₂

3: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

4: 40 percent / BF₃*Et₂O / CH₂Cl₂

5: 2,6-lutidine / CH₂Cl₂

6: sodium cyanoborohydride; TMSCl / acetonitrile

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; chloro-trimethyl-silane; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; 4 Angstroem MS; boron trifluoride diethyl etherate; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; In diethyl ether; dichloromethane; acetonitrile; 2: Sharpless asymmetric epoxidation / 4: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6

Reference yield:

: (E)-5-Bromo-hexa-2,5-dien-1-ol

: 346701-76-6
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: (+)-diisopropyl L-(+)-tartrate; TBHP; 4 Angstroem MS / Ti(Oi-Pr)4 / CH₂Cl₂

2: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

3: 40 percent / BF₃*Et₂O / CH₂Cl₂

4: 2,6-lutidine / CH₂Cl₂

5: sodium cyanoborohydride; TMSCl / acetonitrile

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; chloro-trimethyl-silane; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; 4 Angstroem MS; boron trifluoride diethyl etherate; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In dichloromethane; acetonitrile; 1: Sharpless asymmetric epoxidation / 3: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6

Reference yield:

: 2-(5-bromo-hex-5-en-2-ynyloxy)-tetrahydro-pyran

: 346701-76-6
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: TsOH / methanol

2: Red-Al / diethyl ether

3: (+)-diisopropyl L-(+)-tartrate; TBHP; 4 Angstroem MS / Ti(Oi-Pr)4 / CH₂Cl₂

4: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

5: 40 percent / BF₃*Et₂O / CH₂Cl₂

6: 2,6-lutidine / CH₂Cl₂

7: sodium cyanoborohydride; TMSCl / acetonitrile

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; chloro-trimethyl-silane; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; 4 Angstroem MS; boron trifluoride diethyl etherate; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; In methanol; diethyl ether; dichloromethane; acetonitrile; 3: Sharpless asymmetric epoxidation / 5: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6