(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

Base Information

Chemical Name:(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide
CAS No.:233679-23-7
Molecular Formula:C₁₈H₂₁NO₈S
Molecular Weight:411.433
Hs Code.:

Synonyms:(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

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Chemical Property of (2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

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Technology Process of (2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

There total 13 articles about (2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide 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: 72.0%

: 233679-21-5
(2S,3S,4S,5S)-5-hydroxymethyl-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

: 233679-23-7
(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 - 20 ℃; for 1h;
DOI:10.1021/jo990195x

Reference yield:

: 873-55-2
sodium benzenesulfonate

: 233679-23-7
(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

Guidance literature:: Multi-step reaction with 10 steps

1: 74 percent / monopotassium phosphate buffer / H₂O / 1 h / 20 °C

2: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C

3: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η³-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication

4: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH₂Cl₂; H₂O / 24 h / 20 °C

5: 92 percent / PPTS / CH₂Cl₂ / 24 h / 35 °C

6: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h

7: lead tetraacetate; water / acetone / 1.5 h / 0 - 20 °C

8: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 5 h / 20 °C

9: 40 mg / lithium borohydride / tetrahydrofuran / 1 h / -10 - 20 °C

10: 72 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 - 20 °C

With lead(IV) acetate; lithium borohydride; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 1: Michael addition / 2: Alkylation / 3: Alkylation / 4: Oxidation / 5: ketalization / 6: Hydrogenolysis / 7: Decarboxylation / 8: Esterification / 9: Reduction / 10: Oxidation;
DOI:10.1021/jo990195x

Reference yield:

: 108-98-5
thiophenol

: 233679-23-7
(2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran acetonide

Guidance literature:: Multi-step reaction with 11 steps

2: hydrogen peroxide / acetic acid

3: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C

4: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η³-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication

5: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH₂Cl₂; H₂O / 24 h / 20 °C

6: 92 percent / PPTS / CH₂Cl₂ / 24 h / 35 °C

7: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h

8: lead tetraacetate; water / acetone / 1.5 h / 0 - 20 °C

9: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 5 h / 20 °C

10: 40 mg / lithium borohydride / tetrahydrofuran / 1 h / -10 - 20 °C

11: 72 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 - 20 °C

With lead(IV) acetate; lithium borohydride; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; water; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; acetone; acetonitrile; 1: Addition / 2: Oxidation / 3: Alkylation / 4: Alkylation / 5: Oxidation / 6: ketalization / 7: Hydrogenolysis / 8: Decarboxylation / 9: Esterification / 10: Reduction / 11: Oxidation;
DOI:10.1021/jo990195x