N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

Base Information

• Chemical Name: N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide
• CAS No.: 174741-83-4
• Molecular Formula: C₃₃H₃₇NO₈
• Molecular Weight: 575.659

Synonyms:N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

Chemical Property of N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

Chemical Property:

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Technology Process of N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

There total 8 articles about N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide 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: 74.0%

N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-hydroxymethyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide (174741-82-3) → N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.02,4]dec-6-yl]-acetamide (174741-83-4)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 36h;

DOI:10.1021/jo951747o

Reference yield:

benzyl bromide (100-39-0) → N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.02,4]dec-6-yl]-acetamide (174741-83-4)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH, TBAI / tetrahydrofuran; dimethylformamide; paraffin / 24 h

2: 62 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 1 h, 2.) 8 h

3: 95 percent / 1N HCl / tetrahydrofuran / 18 h / 57 °C

4: 33 percent / MS 4 Angstroem, Amberlyst 15 / tetrahydrofuran / 96 h

5: 87 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; H₂O / 0.17 h / -10 °C

6: 74 percent / NaHCO₃, MCPBA / CH₂Cl₂ / 36 h

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; Amberlyst 15; cerium(III) chloride; MS 4 Angstroem; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; paraffin;

DOI:10.1021/jo951747o

Reference yield:

Acetic acid (1S,3S,6R,7S,8S,10S)-10-acetoxy-6-acetylamino-4-oxo-2,9-dioxa-tricyclo[4.3.1.03,8]dec-7-yl ester (144152-64-7) → N-[(1S,2S,4R,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-hydroxymethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.02,4]dec-6-yl]-acetamide (174741-83-4)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / methanol; paraffin / 0.25 h

2: NaH, TBAI / tetrahydrofuran; dimethylformamide; paraffin / 24 h

3: 62 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 1 h, 2.) 8 h

4: 95 percent / 1N HCl / tetrahydrofuran / 18 h / 57 °C

5: 33 percent / MS 4 Angstroem, Amberlyst 15 / tetrahydrofuran / 96 h

6: 87 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; H₂O / 0.17 h / -10 °C

7: 74 percent / NaHCO₃, MCPBA / CH₂Cl₂ / 36 h

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; Amberlyst 15; cerium(III) chloride; MS 4 Angstroem; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; paraffin;

DOI:10.1021/jo951747o

upstream raw materials:

N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-hydroxymethyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide

benzyl bromide

Acetic acid (1S,3S,6R,7S,8S,10S)-10-acetoxy-6-acetylamino-4-oxo-2,9-dioxa-tricyclo[4.3.1.0^3,8]dec-7-yl ester

N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

Downstream raw materials:

N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

N-[(1S,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

N-[(1S,2S,4S,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-iodomethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

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