(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

Base Information

Chemical Name:(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one
CAS No.:122821-84-5
Molecular Formula:C₃₂H₃₈O₄Si
Molecular Weight:514.737
Hs Code.:

Synonyms:(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

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Chemical Property of (2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

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Technology Process of (2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

There total 9 articles about (2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one 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:

: 122821-81-2
2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

: 122821-84-5
(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / amberlyst-15 (H+) / methanol / 4 h / 60 °C

2: 1.) n-Bu₂SnO / 1.) MeOH, 60 deg C, 1 h, 2.) DMF, 100 deg C, 4 h

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 10 min

With oxalyl dichloride; Amberlyst-15 (H+); di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In methanol;
DOI:10.1021/ja00199a031

Reference yield:

: 122821-78-7
(2R,3S,4R,5S,6R)-2-Allyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol

: 122821-84-5
(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: camphorsulfonic acid (CSA) / 1 h / 0 °C

2: 92 percent / toluene / 3 h / Heating

3: 72 percent / n-Bu₃SnH, AIBN / toluene / 3 h / 110 °C

4: 72 percent / amberlyst-15 (H+) / methanol / 4 h / 60 °C

5: 1.) n-Bu₂SnO / 1.) MeOH, 60 deg C, 1 h, 2.) DMF, 100 deg C, 4 h

6: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 10 min

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Amberlyst-15 (H+); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In methanol; toluene;
DOI:10.1021/ja00199a031

Reference yield:

: 122821-79-8
2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-7,8,9-trideoxy-4,5-O-isopropylidene-D-glycero-D-manno-non-8-enitol

: 122821-84-5
(2R,4S,6S)-2-Allyl-4-(benzyloxy)-6-<(tert-butyldiphenylsilyloxy)methyl>dihydro-2H-pyran-3(4H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / toluene / 3 h / Heating

2: 72 percent / n-Bu₃SnH, AIBN / toluene / 3 h / 110 °C

3: 72 percent / amberlyst-15 (H+) / methanol / 4 h / 60 °C

4: 1.) n-Bu₂SnO / 1.) MeOH, 60 deg C, 1 h, 2.) DMF, 100 deg C, 4 h

5: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) 0 deg C, 10 min

With oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Amberlyst-15 (H+); tri-n-butyl-tin hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In methanol; toluene;
DOI:10.1021/ja00199a031