3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

Base Information

Chemical Name:3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
CAS No.:219826-01-4
Molecular Formula:C₁₆H₂₀O₉
Molecular Weight:356.329
Hs Code.:

Synonyms:3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

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Chemical Property of 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

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Technology Process of 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

There total 5 articles about 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol 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: 81.0%

: 108-24-7
acetic anhydride

: 219864-00-3
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

: 219826-01-4
3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; for 72h; Ambient temperature;
DOI:10.1021/jo980517h

Reference yield:

: 219864-01-4
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol

: 219826-01-4
3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / aq. NaOH / methanol; CH₂Cl₂ / 1 h / Ambient temperature

2: 81 percent / TMSOTf / 72 h / Ambient temperature

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;
DOI:10.1021/jo980517h

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 219826-01-4
3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) CeCl₃ / 1) THF, hexane, -78 deg C, 45 min; 2) THF, hexane, -78 deg C, 30 min; 3) THF, hexane, -78 deg C --> rt, 2 h

2: 1.) Et₃SiH, 2.) BF₃OEt₂ / 1) CH₃CN, CH₂Cl₂, -10 deg C; 2) CH₃CN, CH₂Cl₂, -10 deg C, 1 h

3: 99 percent / aq. NaOH / methanol; CH₂Cl₂ / 1 h / Ambient temperature

4: 81 percent / TMSOTf / 72 h / Ambient temperature

With triethylsilane; sodium hydroxide; n-butyllithium; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In methanol; dichloromethane;
DOI:10.1021/jo980517h