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

Base Information

• Chemical Name: (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one
• CAS No.: 400737-93-1
• Molecular Formula: C₂₆H₃₆O₅SSi
• Molecular Weight: 488.72

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

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

Chemical Property:

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

There total 8 articles about (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one 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: 96.0%

(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol (400737-89-5) → (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one (400737-93-1)

Guidance literature:

With phthalic acid dimethyl ester; sodium hydrogencarbonate; In dichloromethane; at 25 ℃; 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,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one (400737-93-1)

Guidance literature:

Multi-step reaction with 6 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

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; 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,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one (400737-93-1)

Guidance literature:

Multi-step reaction with 5 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

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; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0304953

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

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

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

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