(3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol

Base Information

• Chemical Name: (3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol
• CAS No.: 61489-23-4
• Molecular Formula: C18H28O6
• Molecular Weight: 340.417
• Hs Code.: 29329900
• DSSTox Substance ID: DTXSID80428107
• Nikkaji Number: J2.985.416E
• Wikidata: Q82240892
• Mol file: 61489-23-4.mol

Synonyms:61489-23-4;(3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol;SCHEMBL7441773;DTXSID80428107;2-O,3-O:5-O,6-O-Dicyclohexylidene-alpha-D-mannofuranose;(3'aS,4'S,6'R,6'aS)-6'-[(2R)-1,4-dioxaspiro[4.5]decan-2-yl]-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'-ol;(3a'S,4'S,6'R,6a'S)-6'-((R)-1,4-Dioxaspiro[4.5]decan-2-yl)tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'-ol;(3a'S,4'S,6'R,6a'S)-6'-[(2R)-1,4-Dioxaspiro[4.5]decan-2-yl]tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'-ol (non-preferred name)

Chemical Property of (3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol

Chemical Property:

• Melting Point: 120-124 °C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 507.3 °C at 760 mmHg
• Flash Point: 260.6 °C
• PSA: 66.38000
• Density: 1.1440 (rough estimate)
• LogP: 2.22380
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 340.18858861
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

98%min ^*data from raw suppliers

2,3:5,6-DI-O-CYCLOHEXYLIDENE-ALPHA-D-MANNOFURANOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)OCC(O2)C3C4C(C(O3)O)OC5(O4)CCCCC5
• Isomeric SMILES: C1CCC2(CC1)OC[C@@H](O2)[C@@H]3[C@H]4[C@@H]([C@H](O3)O)OC5(O4)CCCCC5

Technology Process of (3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol

There total 12 articles about (3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-ol 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: 100.0%

2,3:5,6-O-dicyclohexylidene D-gulono-lactone (119680-72-7) → 2,3:5,6-di-O-cyclohexylidene-D-gulo-furanose (61084-13-7,61489-23-4)

Guidance literature:

2,3:5,6-O-dicyclohexylidene D-gulono-lactone; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -15 - -10 ℃; for 0.25 - 0.5h;

With water; Rochelle's salt; In tetrahydrofuran; toluene; at 10 - 20 ℃; for 4h;

Reference yield: 86.0%

D-Mannose (530-26-7) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2,3:5,6-di-O-cyclohexylidene-D-manno-furanose (61489-23-4)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 0.5h;

DOI:10.1007/BF00767389

Reference yield:

D-gulono-1,4-lactone (6322-07-2) → 2,3:5,6-di-O-cyclohexylidene-D-gulo-furanose (61084-13-7,61489-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH / benzene / 10 h / Heating

2: DIBAL / tetrahydrofuran; toluene / 1 h / -78 °C

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/ja00275a064

upstream raw materials:

D-Mannose

cyclohexanone

2,3:5,6-O-dicyclohexylidene D-gulono-lactone

2,3:5,6-di-O-cyclohexylidene-D-mannofurano-lactone

Downstream raw materials:

C₂₄H₃₃NO₆

methyl 2-((3aR,4S,5aS,8R,9aS,9bS)-4-((R)-1,2-dihydroxyethyl)octahydrospiro[[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-2,1'-cyclohexan]-8-yl)acetate

C₃₂H₄₄N₂O₁₀

methyl 5-<<(benzyloxycarbonyl)amino>methyl>-N-(2,3:5,6-O-dicyclohexylidene-D-gulofuranosyl)isoxazolidine-3-carboxylate

Refernces

• 1、 Chase, Charles E.,Fang, Francis G.,Lewis, Bryan M.,Wilkie, Gordon D.,Schnaderbeck, Matthew J.,Zhu, Xiaojie. "Process development of halaven: Synthesis of the C1-C13 fragment from d -(-)-gulono-1,4-lactone". . p. 323 - 326. Retrieved 2013/04/10.
• 2、 Kornilov,Glebova,Turik,Bicherova,Zhdanov. "Chloroglycidate synthesis of a precursor of natural 3-deoxy-D-manno- octulosonic acid with combined protective groups". . p. 225 - 229. Retrieved 2007/10/03.