bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide

Base Information

• Chemical Name: bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide
• CAS No.: 128333-80-2
• Molecular Formula: C₂₄H₃₈O₁₀S₂
• Molecular Weight: 550.692

Synonyms:bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide

Chemical Property of bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide

Chemical Property:

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Technology Process of bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide

There total 6 articles about bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide 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: 51.0%

(1S,2S,5R)-(+)-neomenthyl thiol (53273-24-8,196622-67-0,223653-15-4,173006-99-0) + 2,3:4,5-di-O-isopropylidene-1-sulfanyl-1-deoxy-β-D-fructopyranose (604771-74-6) → S-{[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfanyl}-2,3:4,5-di-O-isopropylidene-1-thio-β-D-fructopyranose + bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide (128333-80-2) + <(1S,2S,5R)-2-isopropyl-5-methylctclohexyl> disulphide

Guidance literature:

With iodine; In ethanol; at 20 ℃; for 2h;

DOI:10.1007/s11172-015-0926-2

Reference yield:

Sodium; ((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-methanethiolate → bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide (128333-80-2) + 1-(4-azido-2-nitrophenyl)thio-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (128333-78-8)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 3.5h; Yield given. Yields of byproduct given;

DOI:10.1016/0008-6215(89)85100-6

Reference yield:

4-fluoro-3-nitrophenylazide (28166-06-5) + Sodium; ((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-methanethiolate → bis(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl) disulfide (128333-80-2) + 1-(4-azido-2-nitrophenyl)thio-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose (128333-78-8)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 3.5h; Yield given. Yields of byproduct given;

DOI:10.1016/0008-6215(89)85100-6

upstream raw materials:

4-fluoro-3-nitrophenylazide

(3aR,5aR,8aR,8bS)-3a-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

(1S,2S,5R)-(+)-neomenthyl thiol

2,3:4,5-di-O-isopropylidene-1-sulfanyl-1-deoxy-β-D-fructopyranose

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