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

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran
• CAS No.: 400738-00-3
• Molecular Formula: C₃₃H₅₄O₅SSi₂
• Molecular Weight: 619.026

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 10 articles about (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran 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: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + (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) → (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran (400738-00-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 40 ℃; for 24h;

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

Reference yield: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-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 (400738-00-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 40 ℃; for 24h;

DOI:10.1021/ja0304953

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran (400738-00-3)

Guidance literature:

Multi-step reaction with 8 steps

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

2.1: 92 percent / BCl₃*SMe₂ / CH₂Cl₂ / 0.17 h / 0 °C

3.1: nBu₂SnO / toluene / 6 h / Heating

3.2: 90 percent / CeF / dimethylformamide / 12 h / 70 °C

4.1: 83 percent / nBu₄NI; NaH / dimethylformamide / 1.5 h / 0 °C

5.1: [RhCl(PPh₃)3]; DABCO / methanol; H₂O / 1 h / Heating

5.2: 92 percent / NMO; OsO₄ / acetone; H₂O / 12 h / 25 °C

6.1: 96 percent / DMP; NaHCO₃ / CH₂Cl₂ / 0.17 h / 25 °C

7.1: 91 percent / diethyl ether / 0.17 h / -78 °C

8.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 0 - 40 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; tris(triphenylphosphine)rhodium(I) chloride; phthalic acid dimethyl ester; boron trichloride - methyl sulfide complex; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

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