(5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

Base Information

Chemical Name:(5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside
CAS No.:160765-89-9
Molecular Formula:C₂₂H₂₈O₇
Molecular Weight:404.46
Hs Code.:

Synonyms:

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Chemical Property of (5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

Chemical Property:

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Technology Process of (5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

There total 1 articles about (5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside 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:

: 114884-40-1
(S)-3,4-O-isopropylidene-3,4-dihydroxybutyltriphenylphosphonium iodide

: 57492-91-8
1-O-benzoyl 2,3-O-isopropylidene-α-D-lyxopentodialdehydo-1,4-furanoside

: 160765-89-9
(5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

Guidance literature:: With sodium hexamethyldisilazane; Yield given. Multistep reaction; 1.) toluene, r.t., 10 min, 2.) toluene, -60 deg C up to r.t.;

Reference yield:

: 160765-89-9
(5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

: 160766-09-6
methyl (methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-5-dichloroacetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 16 steps

1: 96 percent / CH₃ONa / methanol / 1 h / Ambient temperature

2: 93 percent / NaBH₄ / ethanol / 1 h / 55 °C

3: 88 percent / Et₃N / acetonitrile / 1 h / -35 °C

4: 89 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 12.3 h / -10 °C

5: 77 percent / NaH, MgSO₄ / CH₂Cl₂ / 10 h

6: 92 percent / 0.3M BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

7: 83 percent / TsOH*H₂O / pyridine; H₂O / 12 h / 80 °C

8: 82 percent / TsOH*H₂O / methanol / 4 h

9: 63 percent / (Bu₃Sn)2O, 2M Br₂ / CH₂Cl₂ / 1 h / 0 °C

10: 60 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 °C

11: 25 percent / satd. HCl / 1.5 h / -10 °C

12: 92 percent / pyridine / 12 h / Ambient temperature

13: 94 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 5 h / 3000.2 Torr / Ambient temperature

14: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C up to r.t.

15: H₂O₂, NaClO₂, NaH₂PO₄ / acetonitrile; H₂O / 4 h

16: diethyl ether

With pyridine; hydrogenchloride; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; bromine; sodium methylate; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

Reference yield:

: 160765-89-9
(5Z)-1-O-benzoyl-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranoside

: 160766-08-5
methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-3,5-dideoxy-5-dichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

Guidance literature:: Multi-step reaction with 13 steps

1: 96 percent / CH₃ONa / methanol / 1 h / Ambient temperature

2: 93 percent / NaBH₄ / ethanol / 1 h / 55 °C

3: 88 percent / Et₃N / acetonitrile / 1 h / -35 °C

4: 89 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 12.3 h / -10 °C

5: 77 percent / NaH, MgSO₄ / CH₂Cl₂ / 10 h

6: 92 percent / 0.3M BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

7: 83 percent / TsOH*H₂O / pyridine; H₂O / 12 h / 80 °C

8: 82 percent / TsOH*H₂O / methanol / 4 h

9: 63 percent / (Bu₃Sn)2O, 2M Br₂ / CH₂Cl₂ / 1 h / 0 °C

10: 60 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 °C

11: 25 percent / satd. HCl / 1.5 h / -10 °C

12: 92 percent / pyridine / 12 h / Ambient temperature

13: 94 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 5 h / 3000.2 Torr / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen; bromine; sodium methylate; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;