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

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3-ol
CAS No.:197165-05-2
Molecular Formula:C₄₀H₅₂O₅S
Molecular Weight:644.916
Hs Code.:

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

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

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

There total 7 articles about (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-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: 85.0%

: 197165-01-8
(2R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-dicyclohexylmethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 197165-05-2
(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.25h;
DOI:10.1021/jo971233k

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 197165-05-2
(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / camphorsulfonic acid / dimethylformamide / 3 h / 57 °C / 20 Torr

2: 93 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature

3: 85 percent / triethylsilane, TFA / CH₂Cl₂ / 0.25 h

With triethylsilane; camphor-10-sulfonic acid; sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k

Reference yield:

: Dicyclohexyl-methanethiol

: 197165-05-2
(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 49 percent / TMSOTf / CH₂Cl₂ / 16 h / Ambient temperature

2: 100 percent / NaOMe / CH₂Cl₂; methanol / 3 h

3: 100 percent / camphorsulfonic acid / dimethylformamide / 3 h / 57 °C / 20 Torr

4: 93 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature

5: 85 percent / triethylsilane, TFA / CH₂Cl₂ / 0.25 h

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k