((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

Base Information

Chemical Name:((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester
CAS No.:397870-74-5
Molecular Formula:C₄₇H₇₁NO₁₁S
Molecular Weight:858.147
Hs Code.:

((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

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Chemical Property of ((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

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Technology Process of ((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

There total 18 articles about ((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl 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:

: 100-39-0
benzyl bromide

: 397870-74-5
((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: nBu₂SnO / toluene / Heating

1.2: 95 percent / CsF / dimethylformamide / 50 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3.1: toluene / 100 °C

4.1: 71 percent / DIBAL-H / toluene / -78 °C

5.1: DBU / CH₂Cl₂ / 0 °C

6.1: 60 percent / K₂CO₃ / xylene / 140 h / 140 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂

8.1: Zn(BH₄)2 / diethyl ether / 0 °C

9.1: 91 percent / 6M aq. HCl / tetrahydrofuran / 20 °C

10.1: toluene / 100 °C

11.1: CSA / 50 °C

12.1: DIBAL-H / toluene / -78 °C

13.1: NaHCO₃ / methanol

14.1: MsCl; Et₃N / CH₂Cl₂

14.2: 85 percent / LiBr / acetone

15.1: 86 percent / n-BuLi / tetrahydrofuran / -78 °C

With hydrogenchloride; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; 2.1: Swern oxidation / 3.1: Wittig reaction / 6.1: Overman rearrangement / 10.1: Wittig olefination;
DOI:10.1021/ol0171620

Reference yield:

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

: 397870-74-5
((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: nBu₂SnO / toluene / Heating

1.2: 95 percent / CsF / dimethylformamide / 50 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3.1: toluene / 100 °C

4.1: 71 percent / DIBAL-H / toluene / -78 °C

5.1: DBU / CH₂Cl₂ / 0 °C

6.1: 60 percent / K₂CO₃ / xylene / 140 h / 140 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂

8.1: Zn(BH₄)2 / diethyl ether / 0 °C

9.1: 91 percent / 6M aq. HCl / tetrahydrofuran / 20 °C

10.1: toluene / 100 °C

11.1: CSA / 50 °C

12.1: DIBAL-H / toluene / -78 °C

13.1: NaHCO₃ / methanol

14.1: MsCl; Et₃N / CH₂Cl₂

14.2: 85 percent / LiBr / acetone

15.1: 86 percent / n-BuLi / tetrahydrofuran / -78 °C

With hydrogenchloride; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; 2.1: Swern oxidation / 3.1: Wittig reaction / 6.1: Overman rearrangement / 10.1: Wittig olefination;
DOI:10.1021/ol0171620

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 397870-74-5
((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: iPr₂NEt / CH₂Cl₂

1.2: 90 percent / AcOH / H₂O

2.1: nBu₂SnO / toluene / Heating

2.2: 95 percent / CsF / dimethylformamide / 50 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.1: toluene / 100 °C

5.1: 71 percent / DIBAL-H / toluene / -78 °C

6.1: DBU / CH₂Cl₂ / 0 °C

7.1: 60 percent / K₂CO₃ / xylene / 140 h / 140 °C

8.1: O₃ / CH₂Cl₂ / -78 °C

8.2: Me₂S / CH₂Cl₂

9.1: Zn(BH₄)2 / diethyl ether / 0 °C

10.1: 91 percent / 6M aq. HCl / tetrahydrofuran / 20 °C

11.1: toluene / 100 °C

12.1: CSA / 50 °C

13.1: DIBAL-H / toluene / -78 °C

14.1: NaHCO₃ / methanol

15.1: MsCl; Et₃N / CH₂Cl₂

15.2: 85 percent / LiBr / acetone

16.1: 86 percent / n-BuLi / tetrahydrofuran / -78 °C

With hydrogenchloride; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; 3.1: Swern oxidation / 4.1: Wittig reaction / 7.1: Overman rearrangement / 11.1: Wittig olefination;
DOI:10.1021/ol0171620