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

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-heptanoic acid methyl ester
CAS No.:346701-79-9
Molecular Formula:C₂₉H₄₅BrO₆Si
Molecular Weight:597.662
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-heptanoic acid methyl ester

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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-heptanoic acid methyl ester

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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-heptanoic acid methyl ester

There total 14 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-heptanoic acid methyl ester 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

: 346701-79-9
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Red-Al / diethyl ether

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

3.1: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

4.1: 40 percent / BF₃*Et₂O / CH₂Cl₂

5.1: 2,6-lutidine / CH₂Cl₂

6.1: sodium cyanoborohydride; TMSCl / acetonitrile

7.1: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

7.2: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol

8.1: diethyl ether

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; 2.1: Sharpless asymmetric epoxidation / 4.1: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6

Reference yield:

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

: 346701-79-9
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2.1: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

3.1: 40 percent / BF₃*Et₂O / CH₂Cl₂

4.1: 2,6-lutidine / CH₂Cl₂

5.1: sodium cyanoborohydride; TMSCl / acetonitrile

6.1: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

6.2: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol

7.1: diethyl ether

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 diethyl ether; dichloromethane; acetonitrile; 1.1: Sharpless asymmetric epoxidation / 3.1: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6

Reference yield:

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

: 346701-79-9
(3R,4R,7S)-7-[(2R,3S)-3-(2-Bromo-allyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4-methyl-5-methylene-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: TsOH / methanol

2.1: Red-Al / diethyl ether

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

4.1: 70 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

5.1: 40 percent / BF₃*Et₂O / CH₂Cl₂

6.1: 2,6-lutidine / CH₂Cl₂

7.1: sodium cyanoborohydride; TMSCl / acetonitrile

8.1: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

8.2: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol

9.1: diethyl ether

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; 3.1: Sharpless asymmetric epoxidation / 5.1: Sakurai reaction;
DOI:10.1016/S0040-4039(01)00450-6