tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-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-bromo-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate
• CAS No.: 397870-64-3
• Molecular Formula: C₂₇H₄₀BrNO₇
• Molecular Weight: 570.521

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 24 articles about tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-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: 85.0%

tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate (397870-73-4) → tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate (397870-64-3)

Guidance literature:

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

With lithium bromide; In acetone; Further stages.;

DOI:10.1021/ol0171620

Reference yield:

1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose (104487-62-9) → tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate (397870-64-3)

Guidance literature:

Multi-step reaction with 15 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

14.1: triethylamine / CH₂Cl₂ / 0.33 h / 25 °C

15.1: 72.2 mg / LiBr / tetrahydrofuran / 0.67 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; lithium bromide; 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:

6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose (397870-67-6) → tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate (397870-64-3)

Guidance literature:

Multi-step reaction with 14 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

13.1: triethylamine / CH₂Cl₂ / 0.33 h / 25 °C

14.1: 72.2 mg / LiBr / tetrahydrofuran / 0.67 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; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 1.1: Swern oxidation / 5.1: Overman rearrangement;

DOI:10.1246/bcsj.75.1927

upstream raw materials:

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

Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

di-tert-butyl dicarbonate

benzyl bromide

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