(2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol
• CAS No.: 400737-98-6
• Molecular Formula: C₂₇H₄₀O₅SSi
• Molecular Weight: 504.763

Synonyms:(2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

There total 10 articles about (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-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: 91.0%

methylmagnesium bromide (75-16-1) + (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one (400737-93-1) → (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol (400737-98-6)

Guidance literature:

In diethyl ether; at -78 ℃; for 0.166667h;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol (400737-98-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 92 percent / boron trichloride dimethylsulfide / CH₂Cl₂ / 0.5 h / 0 °C

3.1: nBu₂SnO / toluene / 6 h / Heating

3.2: 68 percent / cesium fluoride / dimethylformamide / 12 h / 70 °C

4.1: NaH / dimethylformamide / 25 °C

4.2: 83 percent / tetra-n-butylammonium iodide / dimethylformamide / 25 °C

5.1: (Ph₃P)3RhCl; 1,4-diazabicyclo[2.2.2]octane / methanol; H₂O / 2 h / Heating

5.2: 92 percent / N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 25 °C

6.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

7.1: diethyl ether / 0.17 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; Wilkinson's catalyst; boron trichloride - methyl sulfide complex; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0304953

Reference yield:

S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside (331456-83-8) → (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol (400737-98-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / boron trichloride dimethylsulfide / CH₂Cl₂ / 0.5 h / 0 °C

2.1: nBu₂SnO / toluene / 6 h / Heating

2.2: 68 percent / cesium fluoride / dimethylformamide / 12 h / 70 °C

3.1: NaH / dimethylformamide / 25 °C

3.2: 83 percent / tetra-n-butylammonium iodide / dimethylformamide / 25 °C

4.1: (Ph₃P)3RhCl; 1,4-diazabicyclo[2.2.2]octane / methanol; H₂O / 2 h / Heating

4.2: 92 percent / N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 25 °C

5.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

6.1: diethyl ether / 0.17 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; boron trichloride - methyl sulfide complex; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0304953

upstream raw materials:

methylmagnesium bromide

(2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one

t-butyldimethylsiyl triflate

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

(2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran

(2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol

(2S,3S,4R,5S,6S)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran

(2S,3R,4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

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