tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

Base Information

Chemical Name:tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate
CAS No.:397870-73-4
Molecular Formula:C₂₇H₄₁NO₈
Molecular Weight:507.624
Hs Code.:

Synonyms:tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

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Chemical Property of tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

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Technology Process of tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

There total 22 articles about tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate 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:

: 104487-62-9
1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose

: 397870-73-4
tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

Guidance literature:: Multi-step reaction with 13 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

3.1: 98 percent / toluene / 17 h / 100 °C

4.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

5.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

7.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

7.2: Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

8.1: 93 percent / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

9.1: aqueous HCl / tetrahydrofuran / 3 h / 25 °C

10.1: benzoic acid / CH₂Cl₂ / 2.5 h / 25 °C

11.1: 641 mg / camphorsulfonic acid / benzene / 13 h / 50 °C

12.1: DIBAL-H / toluene / 4 h / -78 °C

13.1: 223 mg / NaHCO₃ / methanol / 12 h / 25 °C

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 2.1: Swern oxidation / 6.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 397870-67-6
6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose

: 397870-73-4
tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: 98 percent / toluene / 17 h / 100 °C

3.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

4.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

6.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

6.2: Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

7.1: 93 percent / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

8.1: aqueous HCl / tetrahydrofuran / 3 h / 25 °C

9.1: benzoic acid / CH₂Cl₂ / 2.5 h / 25 °C

10.1: 641 mg / camphorsulfonic acid / benzene / 13 h / 50 °C

11.1: DIBAL-H / toluene / 4 h / -78 °C

12.1: 223 mg / NaHCO₃ / methanol / 12 h / 25 °C

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 1.1: Swern oxidation / 5.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 475291-30-6
6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

: 397870-73-4
tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / toluene / 17 h / 100 °C

2.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

3.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

5.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

5.2: Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

6.1: 93 percent / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

7.1: aqueous HCl / tetrahydrofuran / 3 h / 25 °C

8.1: benzoic acid / CH₂Cl₂ / 2.5 h / 25 °C

9.1: 641 mg / camphorsulfonic acid / benzene / 13 h / 50 °C

10.1: DIBAL-H / toluene / 4 h / -78 °C

11.1: 223 mg / NaHCO₃ / methanol / 12 h / 25 °C

With hydrogenchloride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 4.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927