(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

Base Information

Chemical Name:(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone
CAS No.:118246-95-0
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

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Chemical Property of (2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

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Technology Process of (2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

There total 2 articles about (2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone 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: 54.0%

: C₁₆H₁₈O₅

: 74-88-4
methyl iodide

: 118246-95-0
(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

Guidance literature:: With lithium diisopropyl amide;
DOI:10.1021/jo00262a007

Reference yield:

: 128685-03-0
(2R,8R)-5-O-(tert-butyldimethylsilyl)-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

: 118246-95-0
(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: HF / acetonitrile / 60 h / Ambient temperature

2: trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 3 h

With trifluorormethanesulfonic acid; hydrogen fluoride; In dichloromethane; cyclohexane; acetonitrile;
DOI:10.1021/ja00170a024

Reference yield:

: 118246-95-0
(2R,8R)-5-O-benzyl-2,8-dimethyl-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone

: 128685-08-5,128777-59-3
C₈₂H₁₄₉NO₁₂S₂Si₃

Guidance literature:: Multi-step reaction with 11 steps

1: 1.0 N aq. NaOH / tetrahydrofuran; methanol / 0.17 h

2: NaH / dimethylformamide / 0.67 h / 0 - 20 °C

3: 98 percent / H₂ / 5percent Pd(OH)2/C / ethyl acetate / 13 h / 760 Torr

4: 293 mg / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h

5: L-Selectride / tetrahydrofuran / 1.5 h / -78 °C

6: BF₃*OEt₂ / CH₂Cl₂ / 1.) from -78 to 0 deg C, 70 min, 2.) RT, 13 h

7: 93 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

8: 69 percent / I₂, PPh₃, pyridine / benzene / 1.) 0 deg C, 1 h, 2.) RT, 6 h

9: 100 percent / Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

10: 1.) n-BuLi / 1.) THF, hexanes, 0 deg C, 40 min, 2.) a) -78 deg C, 25 min, b) 0 deg C, 3 h

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; iodine; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00170a024