allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

Base Information

Chemical Name:allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside
CAS No.:244612-04-2
Molecular Formula:C₁₈H₂₄O₁₀S₂
Molecular Weight:464.515
Hs Code.:

Synonyms:allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

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Chemical Property of allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

Chemical Property:

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Technology Process of allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

There total 1 articles about allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside 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: 80.0%

: 93382-48-0
allyl 4,6-O-benzylidene-α-D-glucopyranoside

: 124-63-0
methanesulfonyl chloride

: 244612-04-2
allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

Guidance literature:: In pyridine; at 21 ℃; for 6h;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3

Reference yield: 82.0%

: 244612-04-2
allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

: 100-51-6,185532-71-2
benzyl alcohol

: 128241-14-5
allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

: 244612-05-3
allyl 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranoside

Guidance literature:: With sodium; at 21 - 90 ℃; for 15.5h;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3

Reference yield:

: 244612-04-2
allyl 4,6-O-benzylidene-2,3-bis-O-(methanesulfonyl)-α-D-glucopyranoside

: (Z)-2,3,4-tri-O-benzyl-6-deoxy-5-O-[(4-methylphenyl)sulfonyl]-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

Guidance literature:: Multi-step reaction with 9 steps

1: 82 percent / Na / 15.5 h / 21 - 90 °C

2: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 60 °C

3: 75 percent / LiAlH₄; Me₃SiBr / diethyl ether / 0.5 h / Heating

4: 75 percent / pyridine / 4 h / 22 °C

5: 92 percent / LiAlH₄ / diethyl ether / 2 h / Heating

6: {Ir(cod)[PMePh₂]2}PF₆-H₂ / tetrahydrofuran / 21 °C

7: HgO; HgCl₂ / acetone; H₂O / 0.25 h / 21 °C

8: 13 percent / pyridinium p-toluenesulfonate; molecular sieves 3 Angstroem / CH₂Cl₂ / 72 h / 22 °C

9: pyridine / 48 h / 22 °C

With lithium aluminium tetrahydride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl bromide; 3 A molecular sieve; hydrogen; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; acetone; 1: Substitution / 2: Aralkylation / 3: Reduction / 4: Acylation / 5: Reduction / 6: Isomerization / 7: Hydrolysis / 8: Condensation / 9: Acylation;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3