(2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

Base Information

• Chemical Name: (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide
• CAS No.: 233679-08-8
• Molecular Formula: C₅₀H₄₇NO₁₅S
• Molecular Weight: 933.987

Synonyms:(2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

Chemical Property of (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

There total 10 articles about (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-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: 92.0%

2,2-dimethoxy-propane (77-76-9) + (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran (233679-17-9) → (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide (233679-08-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 35 ℃; for 24h;

DOI:10.1021/jo990195x

Reference yield:

sodium benzenesulfonate (873-55-2) → (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide (233679-08-8)

Guidance literature:

Multi-step reaction with 5 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

With di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; 1: Michael addition / 2: Alkylation / 3: Alkylation / 4: Oxidation / 5: ketalization;

DOI:10.1021/jo990195x

Reference yield:

thiophenol (108-98-5) → (2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide (233679-08-8)

Guidance literature:

Multi-step reaction with 6 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

With di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; acetic acid; 1: Addition / 2: Oxidation / 3: Alkylation / 4: Alkylation / 5: Oxidation / 6: ketalization;

DOI:10.1021/jo990195x

upstream raw materials:

2,2-dimethoxy-propane

(2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran

sodium benzenesulfonate

thiophenol

Downstream raw materials:

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

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

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

(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

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