(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran
CAS No.:214476-16-1
Molecular Formula:C₃₄H₃₆O₄S
Molecular Weight:540.723
Hs Code.:

Synonyms:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

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Chemical Property of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

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Technology Process of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

There total 5 articles about (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-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: 95.0%

: 4551-15-9
phenylthiotrimethylsilane

: 214476-15-0
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-methyl-tetrahydro-pyran

: 214476-16-1
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃;
DOI:10.1055/s-1998-3140

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 214476-16-1
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / NaOH, H₂O, Et₃NBnCl / benzene / 5 h / Ambient temperature

2: 78 percent / Bu₃SnH, AIBN / benzene / Heating

3: NIS / 48 h / Ambient temperature

4: Bu₃SnH, AIBN

5: 95 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

With sodium hydroxide; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; N-benzyl-N,N,N-triethylammonium chloride; water; tri-n-butyl-tin hydride; In dichloromethane; benzene;
DOI:10.1055/s-1998-3140

Reference yield:

: 162428-31-1
3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-1,2-C-methylene-D-glycero-D-gulohexitol

: 214476-16-1
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methyl-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: NIS / 48 h / Ambient temperature

2: Bu₃SnH, AIBN

3: 95 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane;
DOI:10.1055/s-1998-3140