(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane
CAS No.:260978-83-4
Molecular Formula:C₃₀H₅₁NO₇Si
Molecular Weight:565.823
Hs Code.:

(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

There total 8 articles about (4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane 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:

: 24424-99-5
di-tert-butyl dicarbonate

: 260978-81-2
(E)-(1R,4R)-4-Benzyloxymethoxy-1-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-enylamine

: 260978-83-4
(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With triethylamine; In diethyl ether; at 20 ℃; for 14h;
DOI:10.1039/a905772b

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 260978-83-4
(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 41 percent / DIPEA / CH₂Cl₂ / 15 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 90 percent / LiCl; DBU / acetonitrile / 20 h

4.1: 99 percent / Zn(BH₄)2 / diethyl ether / 2.5 h / -35 °C

5.1: BuLi / tetrahydrofuran / 0.25 h / 0 °C

5.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 91 percent / xylene / 9.5 h / Heating

7.1: Ba(OH)2 / methanol / 19 h / 20 °C

8.1: NEt₃ / diethyl ether / 14 h / 20 °C

With barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; xylene; 1.1: Etherification / 2.1: Metallation / 2.2: Acylation / 3.1: Condensation / 4.1: Reduction / 5.1: Metallation / 5.2: Addition / 6.1: Rearrangement / 7.1: Deacylation / 8.1: Acylation;
DOI:10.1039/a905772b

Reference yield:

: 96823-34-6
Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

: 260978-83-4
(4S,5S)-4-[(1R,4R,2E)-1-(tert-Butoxycarbonylamino)-4-benzyloxymethoxypent-2-enyl]-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / LiCl; DBU / acetonitrile / 20 h

2.1: 99 percent / Zn(BH₄)2 / diethyl ether / 2.5 h / -35 °C

3.1: BuLi / tetrahydrofuran / 0.25 h / 0 °C

3.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

4.1: 91 percent / xylene / 9.5 h / Heating

5.1: Ba(OH)2 / methanol / 19 h / 20 °C

6.1: NEt₃ / diethyl ether / 14 h / 20 °C

With barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; xylene; 1.1: Condensation / 2.1: Reduction / 3.1: Metallation / 3.2: Addition / 4.1: Rearrangement / 5.1: Deacylation / 6.1: Acylation;
DOI:10.1039/a905772b