(2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 133329-88-1
• Molecular Formula: C₃₂H₃₈O₅
• Molecular Weight: 502.651
• Mol file: 133329-88-1.mol

Synonyms:(2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol

There total 12 articles about (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-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%

(2R,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one (133329-87-0) → (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol (133329-88-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -20 ℃; for 4h;

DOI:10.1016/S0040-4039(00)71216-0

Reference yield:

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one (62396-80-9) → (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol (133329-88-1)

Guidance literature:

Multi-step reaction with 10 steps

1: LDA / tetrahydrofuran / 2 h / -78 °C

2: 69 percent / BH₃-SMe₂ / tetrahydrofuran / 2 h / 23 - 65 °C

3: 82 percent / pyridine / CH₂Cl₂ / 96 h / 23 °C

4: 87 percent / DMEU, NaH / tetrahydrofuran / 24 h / -10 - 23 °C

5: 88 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

6: 83 percent / (COCl)2, DMSO, NEt₃ / CH₂Cl₂ / 1.5 h / -50 °C

7: 1) n-butyllithium, 2) ZnBr₂ / 1) Et₂O, -20 deg C, 2h, 2) Et₂O, -78 deg C to -20 deg C

8: 73 percent / tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂ / 2.5 h / 23 °C

9: 51 percent / BF₃*Et₂O / diethyl ether / 1.5 h / 0 - 23 °C

10: 65 percent / NaBH₄ / methanol / 4 h / -20 °C

With pyridine; 1,3-dimethyl-2-imidazolidinone; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; zinc dibromide; lithium diisopropyl amide; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)71216-0

Reference yield:

2-Bromo-4-methyl-furan (78259-59-3) → (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol (133329-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) n-butyllithium, 2) ZnBr₂ / 1) Et₂O, -20 deg C, 2h, 2) Et₂O, -78 deg C to -20 deg C

2: 73 percent / tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂ / 2.5 h / 23 °C

3: 51 percent / BF₃*Et₂O / diethyl ether / 1.5 h / 0 - 23 °C

4: 65 percent / NaBH₄ / methanol / 4 h / -20 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; zinc dibromide; bis(acetylacetonato) oxovanadium(IV); In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)71216-0

upstream raw materials:

(2R,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

2-Bromo-4-methyl-furan

trityl chloride

Downstream raw materials:

(2S,3R,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran

(2S,3S,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran

(2R,3S,6S)-3,6-Dimethoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran