(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:319922-04-8
Molecular Formula:C₂₅H₃₀O₅S
Molecular Weight:442.576
Hs Code.:

Synonyms:(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 5 articles about (2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 97.0%

: 100-39-0
benzyl bromide

: 319922-00-4
ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 319922-04-8
(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)01497-0

Reference yield:

: 7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3
ethyl 1-thio-α-D-mannopyranoside

: 319922-04-8
(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂SnO / methanol

1.2: 31 percent / tetrabutylammonium bromide

2.1: 65 percent / p-TsOH / dimethylformamide

3.1: 97 percent / NaH / dimethylformamide

With sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; 1.1: stannylation / 1.2: allylation / 2.1: Etherification / 3.1: Etherification;
DOI:10.1016/S0040-4039(00)01497-0

Reference yield:

: 319921-96-5
(2R,3S,4S,5R,6R)-4-Allyloxy-2-ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

: 319922-04-8
(2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / p-TsOH / dimethylformamide

2: 97 percent / NaH / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Etherification / 2: Etherification;
DOI:10.1016/S0040-4039(00)01497-0