(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

Base Information

Chemical Name:(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose
CAS No.:107441-60-1
Molecular Formula:C₃₆H₅₀O₈Si
Molecular Weight:638.874
Hs Code.:

(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

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Chemical Property of (9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

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Technology Process of (9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

There total 7 articles about (9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose 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:

: 3587-60-8
Benzyloxymethyl chloride

: 107441-60-1,107493-81-2
(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

Guidance literature:: Multi-step reaction with 6 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 h / 0 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; lithium diisopropyl amide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00385a024

Reference yield:

: 94118-99-7
1-O-benzyl-2,3-O-isopropylidene-β-L-gulofuranose

: 107441-60-1,107493-81-2
(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

2: CH₂Cl₂ / 1 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane;
DOI:10.1021/jo00385a024

Reference yield:

: 107441-54-3,121793-81-5
(3R)-methyl 2-<(benzyloxy)methyl>-3-hydroxybutyrate

: 107441-60-1,107493-81-2
(9ξ)-benzyl (E)-9-<(benzyloxy)methyl>-10-O-(tert-butyldimethylsilyl)-6,7,9,11-tetradeoxy-2,3-O-isopropylidene-7-C-methyl-D-glycero-α-D-lyxo-undec-6-enofuranosido-5,5-diulose

Guidance literature:: Multi-step reaction with 5 steps

1: 85.9 percent / imidazole / dimethylformamide / 3 h

2: 72.9 percent / aq. LiOH / methanol / 81 h

3: oxalyl chloride, DMF / benzene / 0.42 h

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

5: CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00385a024