3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

Base Information

Chemical Name:3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate
CAS No.:740840-82-8
Molecular Formula:C₆₈H₇₈O₁₄
Molecular Weight:1119.36
Hs Code.:

3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

Synonyms:3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

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Chemical Property of 3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

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Technology Process of 3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

There total 11 articles about 3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate 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: 48.0%

: 102208-53-7
(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

: 740840-81-7
3-((3aS,4S,6R,7R,7aS)-7-Carboxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionic acid

: 740840-82-8
3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1002/anie.200353478

Reference yield:

: 82185-79-3
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 740840-82-8
3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

Guidance literature:: Multi-step reaction with 9 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

2: 503 mg / CH₂Cl₂ / 5 h / 23 °C

3: 88 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 3361.46 Torr

4: 82 percent / NHS; pyridine / toluene / 4 h / 20 °C

5: 71 percent / AIBN / benzene / 5 h / Heating

6: OsO₄; aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

7: 23 mg / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

8: 76 percent / aq. LiOH / tetrahydrofuran / 0 - 20 °C

9: 48 percent / 4-DMAP; DCC / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium chlorite; sodium periodate; dipotassium hydrogenphosphate; 1-hydroxy-pyrrolidine-2,5-dione; osmium(VIII) oxide; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Wittig reaction / 5: Keck allylation;
DOI:10.1002/anie.200353478

Reference yield:

: 132032-75-8
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

: 740840-82-8
3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (4S)-4-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(4-ethanoate))-2,3-O-isopropylidene-4,6,7-trideoxy-β-D-mannooctopyranosid)uronate

Guidance literature:: Multi-step reaction with 8 steps

1: 503 mg / CH₂Cl₂ / 5 h / 23 °C

2: 88 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 3361.46 Torr

3: 82 percent / NHS; pyridine / toluene / 4 h / 20 °C

4: 71 percent / AIBN / benzene / 5 h / Heating

5: OsO₄; aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

6: 23 mg / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

7: 76 percent / aq. LiOH / tetrahydrofuran / 0 - 20 °C

8: 48 percent / 4-DMAP; DCC / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium chlorite; sodium periodate; dipotassium hydrogenphosphate; 1-hydroxy-pyrrolidine-2,5-dione; osmium(VIII) oxide; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol; benzene; 1: Wittig reaction / 4: Keck allylation;
DOI:10.1002/anie.200353478