(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester
• CAS No.: 729596-17-2
• Molecular Formula: C₁₉H₂₄O₁₀S
• Molecular Weight: 444.46
• Mol file: 729596-17-2.mol

Synonyms:(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester

Chemical Property of (4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester

There total 1 articles about (4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl 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:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → (4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester (729596-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: K₃Fe(CN)6; K₂CO₃; (DHQD)2PHAL / potassium osmate; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

With pyridine; thionyl chloride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); methanesulfonamide; In dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo049509t

Reference yield: 81.7%

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester (729596-17-2) → ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate (729596-18-3)

Guidance literature:

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester; With sodium azide; In water; acetone; at 0 - 25 ℃; for 2h;

With sulfuric acid; In diethyl ether; water; at 25 ℃; for 6h;

DOI:10.1021/jo049509t

Reference yield:

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester (729596-17-2) → Acetic acid (1R,2R)-3-acetoxy-1-((2R,3R,4R,5S)-3-acetoxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-2-benzyloxycarbonylamino-propyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

1.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

2.1: LiAlH₄ / tetrahydrofuran / 3 h / 0 - 25 °C

3.1: ammonium formate / Pd/C / methanol / 1 h / Heating

4.1: 0.47 g / NaHCO₃ / methanol; H₂O / 3.5 h / 0 - 25 °C

5.1: 79 percent / pyridine / 8 h / 20 °C

6.1: TFA / H₂O / 2.5 h / 25 °C

With pyridine; lithium aluminium tetrahydride; sodium azide; ammonium formate; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1021/jo049509t

upstream raw materials:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Downstream raw materials:

ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose

3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose