(3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one

Base Information

• Chemical Name: (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one
• CAS No.: 160054-07-9
• Molecular Formula: C₃₁H₃₃NO₇
• Molecular Weight: 531.606
• Mol file: 160054-07-9.mol

Synonyms:

Chemical Property of (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one

There total 16 articles about (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one 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:

Benzyl-carbamic acid (3S,6S,7R,8S)-7,8-bis-(4-methoxy-benzyloxy)-1-oxa-spiro[2.5]oct-4-en-6-yl ester (160054-06-8) → (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one (160054-07-9)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; for 2.5h; -78 deg C -> room temperature;

DOI:10.1016/S0040-4039(00)77001-8

Reference yield:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one (160054-07-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 74 percent / NaH

2: 1.) dimethyldioxirane / 1.) acetone/CH₂Cl₂, 2.) room temperature

3: DMAP, pyridine

4: 91 percent / TBAF / tetrahydrofuran; ethyl acetate

5: 93 percent / pyridine, DMAP

6: 94 percent / KI / dimethylformamide / 2 h / 100 °C

7: 97 percent / AgF, pyridine / 24 h / Ambient temperature

8: 1.) HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone/water, reflux, 4 h, 2.) room temperature, 5 h

9: 92 percent / NaBH₄, CeCl₃ / ethanol / 0.17 h / -78 °C

10: 98 percent / benzene / Heating

11: K₂CO₃ / methanol

12: 85 percent / PDC / acetic acid; ethyl acetate / Ambient temperature

13: 45 percent / Zn, TiCl₄ / tetrahydrofuran / 0.25 h

14: mCPBA, NaHCO₃ / CH₂Cl₂

15: KHMDS, 18-crown-6 / tetrahydrofuran / 2.5 h / -78 deg C -> room temperature

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; titanium tetrachloride; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; potassium carbonate; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; potassium iodide; mercury dichloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)77001-8

Reference yield:

3,4-di-O-(4-methoxybenzyl)-6-O-(triisopropylsilyl)-D-glucal (137895-61-5) → (3aS,6R,7S,7aS)-3-Benzyl-5-hydroxymethyl-6,7-bis-(4-methoxy-benzyloxy)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one (160054-07-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) dimethyldioxirane / 1.) acetone/CH₂Cl₂, 2.) room temperature

2: DMAP, pyridine

3: 91 percent / TBAF / tetrahydrofuran; ethyl acetate

4: 93 percent / pyridine, DMAP

5: 94 percent / KI / dimethylformamide / 2 h / 100 °C

6: 97 percent / AgF, pyridine / 24 h / Ambient temperature

7: 1.) HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone/water, reflux, 4 h, 2.) room temperature, 5 h

8: 92 percent / NaBH₄, CeCl₃ / ethanol / 0.17 h / -78 °C

9: 98 percent / benzene / Heating

10: K₂CO₃ / methanol

11: 85 percent / PDC / acetic acid; ethyl acetate / Ambient temperature

12: 45 percent / Zn, TiCl₄ / tetrahydrofuran / 0.25 h

13: mCPBA, NaHCO₃ / CH₂Cl₂

14: KHMDS, 18-crown-6 / tetrahydrofuran / 2.5 h / -78 deg C -> room temperature

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; titanium tetrachloride; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; potassium iodide; mercury dichloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)77001-8

upstream raw materials:

Benzyl-carbamic acid (3S,6S,7R,8S)-7,8-bis-(4-methoxy-benzyloxy)-1-oxa-spiro[2.5]oct-4-en-6-yl ester

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

3,4-di-O-(4-methoxybenzyl)-6-O-(triisopropylsilyl)-D-glucal

p-methoxybenzyl chloride

Downstream raw materials:

(1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol