(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

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Chemical Name:(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol
CAS No.:383187-79-9
Molecular Formula:C₃₈H₅₄O₆Si
Molecular Weight:634.929
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

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Technology Process of (2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

There total 15 articles about (2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-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: 65.0%

: 383187-78-8
(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-yl]-3-methyl-butan-2-one

: 383187-79-9
(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

Guidance literature:: (R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-yl]-3-methyl-butan-2-one; With 4 A molecular sieve; toluene-4-sulfonic acid hydrazide; In ethanol; for 2h; Heating;

With sodium cyanoborohydride; zinc(II) chloride; In ethanol; for 8h; Heating;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 5673-07-4
2,6-dimethoxytoluene

: 383187-79-9
(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 96 percent / TiCl₄ / benzene / 0.5 h / 0 °C

2.1: 85 percent / mCPBA / CH₂Cl₂ / 20 °C

3.1: 76 percent / BF₃OMe₂ / 3 h / 90 °C

4.1: 99 percent / K₂CO₃ / acetone / 40 h / 20 °C

5.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

5.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C

5.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C

6.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C

7.1: 93 percent / 18 h / 20 °C

8.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂; H₂O; various solvent(s) / 0.5 h

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -78 - 0 °C

10.1: LiOH / diethyl ether / 0.25 h / 20 °C

10.2: 85 percent / diethyl ether / 4 h / 20 °C

11.1: 84 percent / aq. HCl / methanol / 6 h / 20 °C

12.1: p-TsNHNH₂; 4 Angstroem molecular sieves / ethanol / 2 h / Heating

12.2: 65 percent / NaCNBH₃; ZnCl₂ / ethanol / 8 h / Heating

With hydrogenchloride; lithium hydroxide; boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; titanium tetrachloride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetone; acetonitrile; benzene; 1.1: Friedel-Crafts acylation / 2.1: Bayer-Villiger oxidation / 3.1: ortho-Fries rearrangement / 9.1: Swern oxidation / 10.1: Horner-Wadsworth-Emmons reaction / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W

Reference yield:

: 77942-13-3
2',4'-dimethoxy-3'-methylpropiophenone

: 383187-79-9
(2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 85 percent / mCPBA / CH₂Cl₂ / 20 °C

2.1: 76 percent / BF₃OMe₂ / 3 h / 90 °C

3.1: 99 percent / K₂CO₃ / acetone / 40 h / 20 °C

4.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

4.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C

4.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C

5.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C

6.1: 93 percent / 18 h / 20 °C

7.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂; H₂O; various solvent(s) / 0.5 h

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.75 h / -78 - 0 °C

9.1: LiOH / diethyl ether / 0.25 h / 20 °C

9.2: 85 percent / diethyl ether / 4 h / 20 °C

10.1: 84 percent / aq. HCl / methanol / 6 h / 20 °C

11.1: p-TsNHNH₂; 4 Angstroem molecular sieves / ethanol / 2 h / Heating

11.2: 65 percent / NaCNBH₃; ZnCl₂ / ethanol / 8 h / Heating

With hydrogenchloride; lithium hydroxide; boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetone; acetonitrile; 1.1: Bayer-Villiger oxidation / 2.1: ortho-Fries rearrangement / 8.1: Swern oxidation / 9.1: Horner-Wadsworth-Emmons reaction / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W