Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

Base Information

Chemical Name:Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester
CAS No.:119111-10-3
Molecular Formula:C₃₂H₃₂N₂O₅S
Molecular Weight:556.682
Hs Code.:

Synonyms:Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

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Chemical Property of Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

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Technology Process of Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

There total 14 articles about Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester 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: 68.0%

: 119111-07-8
(R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 119111-10-3
Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

Guidance literature:: In dichloromethane; for 2h; Heating;
DOI:10.1021/ja00187a031

Reference yield:

: 214490-84-3
Allyl 2,3,4,6-Tetra-O-acetyl-D-mannopyranoside

: 119111-10-3,119111-36-3
Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2R)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

Guidance literature:: Multi-step reaction with 7 steps

1: AGMP resin / methanol

2: pyridine / 1.5 h / 135 °C

3: LAH, AlCl₃ / CH₂Cl₂; diethyl ether / 0.67 h

4: NaH / dimethylformamide

5: 2.) HgCl₂, HgO, H₂O / 1) Ir(+)(COD)Ph₂PMe*PF₆(-) / 2.) acetone

6: 1.) n-BuLi / 1.) THF, hexane, -20 deg C --> room temp., 1h, 2.) -20 deg C --> room temp., 16h, 3.) 50 deg C, 15 min

7: CH₂Cl₂ / 2 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; AGMP resin; water; sodium hydride; mercury dichloride; mercury(II) oxide; {Ir(COD)[PCH₃(C₆H₅)2]}PF₆; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00187a031

Reference yield:

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 119111-10-3,119111-36-3
Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2R)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / SnCl₄

2: AGMP resin / methanol

3: pyridine / 1.5 h / 135 °C

4: LAH, AlCl₃ / CH₂Cl₂; diethyl ether / 0.67 h

5: NaH / dimethylformamide

6: 2.) HgCl₂, HgO, H₂O / 1) Ir(+)(COD)Ph₂PMe*PF₆(-) / 2.) acetone

7: 1.) n-BuLi / 1.) THF, hexane, -20 deg C --> room temp., 1h, 2.) -20 deg C --> room temp., 16h, 3.) 50 deg C, 15 min

8: CH₂Cl₂ / 2 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; AGMP resin; water; tin(IV) chloride; sodium hydride; mercury dichloride; mercury(II) oxide; {Ir(COD)[PCH₃(C₆H₅)2]}PF₆; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00187a031