N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

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Chemical Name:N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide
CAS No.:639476-10-1
Molecular Formula:C₃₅H₄₁NO₇
Molecular Weight:587.713
Hs Code.:

Synonyms:

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Chemical Property of N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

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Technology Process of N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

There total 12 articles about N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-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:

: 114743-85-0
methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

: 639476-10-1
N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: 74 percent / Ag₂O / CH₂Cl₂

2.1: 87 percent / LiAlH₄ / tetrahydrofuran

3.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

4.1: MgSO₄ / tetrahydrofuran / 2 h / 20 °C

5.1: 1.31 g / tetrahydrofuran / 2 h / 20 °C

6.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

7.1: 76 percent / aq. NMO; OsO₄ / acetone; butan-1-ol / 19 h / 20 °C

8.1: Bu₂SnO / toluene; methanol / 2 h / 85 °C

8.2: 98 percent / TBAB / toluene / 10 h / 80 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

10.1: 80 percent / HCl / methanol / 14 h / 20 °C

11.1: 75 mg / p-toluenesulfonic acid / 0.17 h / 20 °C

With hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; di(n-butyl)tin oxide; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; butan-1-ol;
DOI:10.1021/jo034679b

Reference yield:

: 212832-94-5
Methyl 3,4:5,6-di-O-isopropylidene-2-O-(benzyl)-D-gluconate

: 639476-10-1
N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 87 percent / LiAlH₄ / tetrahydrofuran

2.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

3.1: MgSO₄ / tetrahydrofuran / 2 h / 20 °C

4.1: 1.31 g / tetrahydrofuran / 2 h / 20 °C

5.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

6.1: 76 percent / aq. NMO; OsO₄ / acetone; butan-1-ol / 19 h / 20 °C

7.1: Bu₂SnO / toluene; methanol / 2 h / 85 °C

7.2: 98 percent / TBAB / toluene / 10 h / 80 °C

8.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

9.1: 80 percent / HCl / methanol / 14 h / 20 °C

10.1: 75 mg / p-toluenesulfonic acid / 0.17 h / 20 °C

With hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; di(n-butyl)tin oxide; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; butan-1-ol;
DOI:10.1021/jo034679b

Reference yield:

: 90-80-2,1335-57-5,4253-68-3
D-Glucono-1,5-lactone

: 639476-10-1
N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: 83 percent / p-TsOH hydrate / acetone

2.1: 74 percent / Ag₂O / CH₂Cl₂

3.1: 87 percent / LiAlH₄ / tetrahydrofuran

4.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

5.1: MgSO₄ / tetrahydrofuran / 2 h / 20 °C

6.1: 1.31 g / tetrahydrofuran / 2 h / 20 °C

7.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

8.1: 76 percent / aq. NMO; OsO₄ / acetone; butan-1-ol / 19 h / 20 °C

9.1: Bu₂SnO / toluene; methanol / 2 h / 85 °C

9.2: 98 percent / TBAB / toluene / 10 h / 80 °C

10.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

11.1: 80 percent / HCl / methanol / 14 h / 20 °C

12.1: 75 mg / p-toluenesulfonic acid / 0.17 h / 20 °C

With hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; di(n-butyl)tin oxide; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; butan-1-ol;
DOI:10.1021/jo034679b