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

Base Information

• Chemical Name: Benzyl-carbamic acid (3S,6S,7R,8S)-7,8-bis-(4-methoxy-benzyloxy)-1-oxa-spiro[2.5]oct-4-en-6-yl ester
• CAS No.: 160054-06-8
• Molecular Formula: C₃₁H₃₃NO₇
• Molecular Weight: 531.606
• Mol file: 160054-06-8.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about Benzyl-carbamic acid (3S,6S,7R,8S)-7,8-bis-(4-methoxy-benzyloxy)-1-oxa-spiro[2.5]oct-4-en-6-yl ester 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:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → 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)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; titanium tetrachloride; 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) → 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)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; titanium tetrachloride; 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:

p-methoxybenzyl chloride (824-94-2) → 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)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; titanium tetrachloride; 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

upstream raw materials:

Benzyl-carbamic acid (1S,5R,6R)-5,6-bis-(4-methoxy-benzyloxy)-4-methylene-cyclohex-2-enyl 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:

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