(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

Base Information

Chemical Name:(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol
CAS No.:250599-00-9
Molecular Formula:C₂₅H₃₂O₁₀S₂
Molecular Weight:556.655
Hs Code.:

Synonyms:(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

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Chemical Property of (7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

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Technology Process of (7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

There total 6 articles about (7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol 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: 84.0%

: 124-63-0
methanesulfonyl chloride

: 250598-99-3
(7S)-3,6-anhydro-7-O-benzyl-1,2-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol

: 250599-00-9
(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 100-39-0
benzyl bromide

: 250599-00-9
(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / NaH / dimethylformamide / 0.5 h / 20 °C

2: 86 percent / 60 percent aq. AcOH / 8 h / 20 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With sodium hydride; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Ring cleavage / 3: mesylation;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 201863-41-4
(R)-[(3aR,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-phenyl-methanol

: 250599-00-9
(7S)-3,6-anhydro-7-O-benzyl-4,5-O-isopropylidene-1,2-bis-O-(methylsulfonyl)-7-C-phenyl-D-glycero-D-manno-heptitol

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / PPh₃; DEAD / tetrahydrofuran / 8 h / 0 - 20 °C

2: 93 percent / NaOMe / methanol / 1.5 h / 20 °C

3: 96 percent / NaH / dimethylformamide / 0.5 h / 20 °C

4: 86 percent / 60 percent aq. AcOH / 8 h / 20 °C

5: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With sodium methylate; sodium hydride; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Alkylation / 4: Ring cleavage / 5: mesylation;
DOI:10.1016/S0968-0896(99)00164-9