(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

Base Information

Chemical Name:(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate
CAS No.:107441-76-9
Molecular Formula:C₃₉H₅₀O₇
Molecular Weight:630.822
Hs Code.:

(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

Synonyms:(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

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Chemical Property of (4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

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Technology Process of (4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

There total 17 articles about (4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate 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: 74.5%

: 3282-30-2
pivaloyl chloride

: 107441-74-7
(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-decitol

: 107441-76-9
(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

Guidance literature:: With N',N'-dimethylaminopyridine; In dichloromethane; for 28h;
DOI:10.1021/jo00385a024

Reference yield:

: 107441-63-4
1-O-benzyl-3-deoxy-3-methyl-D-threitol dipivaloate

: 107441-76-9
(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / H₂ / 10percent Pd/C / ethanol / 18 h / 2585.7 Torr

2: oxalyl chloride, DMSO / CH₂Cl₂ / 0.43 h / -78 °C

3: pyridine / benzene / 0.33 h / 5 °C

4: 90.5 percent / N-methoxymorpholine N-oxide, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 10.5 h

5: oxalyl chloride, DMSO / CH₂Cl₂ / -78 - 30 °C

6: CH₂Cl₂ / 1.33 h / -30 - 0 °C

7: 71.4 percent / LiBF₄, p-toluenesulfonic acid / acetone; CH₂Cl₂ / 12 h

8: LiAlH₄ / tetrahydrofuran / 4 h / -78 - 25 °C

9: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h

10: 73.8 percent / BaO, Ba(OH)2 / dimethylformamide / 1.) RT, 0.5 h, 2.) 40 deg C, 34 h

11: 74.5 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 28 h

With pyridine; barium dihydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; N',N'-dimethylaminopyridine; N-methoxymorpholine N-oxide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00385a024

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 107441-76-9
(4ξ,6ξ,7ξ,8ξ)-6,9-anhydro-7-O-benzyl-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-D-glycero-D-threo-4,7-decitol pivaloate

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) lithium diisopropylamide / 1.) THF, 55 min, 2.) THF, 0 deg C, 4 h

2: 85.9 percent / imidazole / dimethylformamide / 3 h

3: 72.9 percent / aq. LiOH / methanol / 81 h

4: oxalyl chloride, DMF / benzene / 0.42 h

5: 1.) n-BuLi / 1.) benzene, hexane, 30 min, 2.) benzene, hexane, 80 deg C, 30 min

6: CH₂Cl₂ / 1.33 h / -30 - 0 °C

7: 71.4 percent / LiBF₄, p-toluenesulfonic acid / acetone; CH₂Cl₂ / 12 h

8: LiAlH₄ / tetrahydrofuran / 4 h / -78 - 25 °C

9: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h

10: 73.8 percent / BaO, Ba(OH)2 / dimethylformamide / 1.) RT, 0.5 h, 2.) 40 deg C, 34 h

11: 74.5 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 28 h

With 1H-imidazole; barium dihydroxide; lithium hydroxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; n-butyllithium; oxalyl dichloride; N',N'-dimethylaminopyridine; toluene-4-sulfonic acid; N,N-dimethyl-formamide; barium(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00385a024