Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

Base Information

Chemical Name:Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester
CAS No.:793673-16-2
Molecular Formula:C₂₀H₂₈O₈S
Molecular Weight:428.504
Hs Code.:

Synonyms:Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

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Chemical Property of Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

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Technology Process of Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

There total 7 articles about Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl 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: 47.0%

: Benzenesulfonic acid (2R,3R)-3-[(2E,4E)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-penta-2,4-dienyl]-oxiranylmethyl ester

: 793673-24-2
Benzenesulfonic acid (2R,3R)-3-[(E)-(4S,5R)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-4,5-dihydroxy-pent-2-enyl]-oxiranylmethyl ester

: 793673-16-2
Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

Guidance literature:: With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 42h;
DOI:10.1021/jo048863o

Reference yield:

: 142-83-6,4488-48-6
trans,trans-2,4-Hexadienal

: 793673-16-2
Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Et₃N; NaI / pentane; acetonitrile / Heating

2.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

2.2: 41 percent / dimethylformamide / -55 - 20 °C

3.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

4.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

5.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

6.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

7.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

With titanium(IV) isopropylate; dmap; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; bromine; potassium carbonate; triethylamine; sodium iodide; In diethyl ether; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; pentane; 5.1: Sharpless asymmetric epoxidation / 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o

Reference yield:

: 114434-56-9
1,(trimethylsilyloxy)hexa-1,3,5-triene

: 793673-16-2
Benzenesulfonic acid (2R,3R)-3-[(E)-(2S,3S)-5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2,3-dihydroxy-pent-4-enyl]-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

1.2: 41 percent / dimethylformamide / -55 - 20 °C

2.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

3.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

4.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

5.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

6.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

With titanium(IV) isopropylate; dmap; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; bromine; potassium carbonate; sodium iodide; In diethyl ether; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 4.1: Sharpless asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o