1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

Base Information

Chemical Name:1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose
CAS No.:209911-85-3
Molecular Formula:C₄₃H₄₄O₈
Molecular Weight:688.818
Hs Code.:

Synonyms:1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

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Chemical Property of 1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

Chemical Property:

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Technology Process of 1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

There total 20 articles about 1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose 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%

: 209911-83-1
4-deoxy-4-ethenylidene-1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-myo-inositol

: 209911-85-3
1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

Guidance literature:: With ozone; In pyridine; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo990086i

Reference yield:

: 209911-52-4
allyl 3-O-benzyl-D-glucopyranoside

: 209911-85-3
1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

Guidance literature:: Multi-step reaction with 19 steps

1: 80 percent / DMAP / pyridine / 8 h / 110 °C

2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 15 min; reflux, 24 h

3: 1.) Ph₃P)3RhCl, DABCO, 2.) HgCl₂, HgO / 1.) PhH, EtOH, H₂O, room temperature, 1 h; reflux, 36 h, 2.) me2CO, H₂O, room temperature, 12 h

4: 93 percent / LiAlH₄ / tetrahydrofuran / 4 h

5: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h

6: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) room temperature, 1 h; reflux, 24 h

7: 92 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

8: 1.) DMSO, (COCl)2, 2) Et₃N / 1.) Ch₂Cl₂, -78 deg C, 30 min, 2.) 6 h

9: 1.) Ph₃P, 2.) Et₃N / 1.) Ch₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C to room temperatur; room temperature, 30 min

10: 85 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

11: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) room temperature, 8 h

12: 94 percent / CSA / CH₂Cl₂; methanol / 36 h

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) Ch₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min; room temperature, 6 h

14: 91 percent / CSA / toluene / 2.5 h

15: 86 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h / Heating

16: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

17: 92 percent / CeCl₃*7H₂O, NaBH₄ / tetrahydrofuran; methanol / 1.) -78 deg C, 1 h, 2.) 0 deg C, 4 h

18: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) reflux, 24 h

19: 80 percent / O₃ / CH₂Cl₂; pyridine / 0.5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo990086i

Reference yield:

: 209911-56-8
2-propenyl 3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucopyranoside

: 209911-85-3
1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 15 min; reflux, 24 h

2: 1.) Ph₃P)3RhCl, DABCO, 2.) HgCl₂, HgO / 1.) PhH, EtOH, H₂O, room temperature, 1 h; reflux, 36 h, 2.) me2CO, H₂O, room temperature, 12 h

3: 93 percent / LiAlH₄ / tetrahydrofuran / 4 h

4: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h

5: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) room temperature, 1 h; reflux, 24 h

6: 92 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

7: 1.) DMSO, (COCl)2, 2) Et₃N / 1.) Ch₂Cl₂, -78 deg C, 30 min, 2.) 6 h

8: 1.) Ph₃P, 2.) Et₃N / 1.) Ch₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C to room temperatur; room temperature, 30 min

9: 85 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

10: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) room temperature, 8 h

11: 94 percent / CSA / CH₂Cl₂; methanol / 36 h

12: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) Ch₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min; room temperature, 6 h

13: 91 percent / CSA / toluene / 2.5 h

14: 86 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h / Heating

15: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

16: 92 percent / CeCl₃*7H₂O, NaBH₄ / tetrahydrofuran; methanol / 1.) -78 deg C, 1 h, 2.) 0 deg C, 4 h

17: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) reflux, 24 h

18: 80 percent / O₃ / CH₂Cl₂; pyridine / 0.5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo990086i