Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

Chemical Name:Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
CAS No.:115533-44-3
Molecular Formula:C₅₀H₅₀N₂O₁₂S
Molecular Weight:903.019
Hs Code.:

Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Synonyms:Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Suppliers and Price of Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Chemical Property of Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Technology Process of Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 23 articles about Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl 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: 90.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 115533-40-9
Phenyl-carbamic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

: 115533-44-3
Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: With tetrafluoroboric acid; In diethyl ether;

Reference yield:

: 34368-66-6
1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose

: 115533-44-3
ethyl O-<4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

2: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

3: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

4: 94 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂; toluene / 45 h / -45 °C

5: K₂CO₃ / methanol / 4 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether

With pyridine; dmap; tetrafluoroboric acid; 4 A molecular sieve; sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; acetic acid; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 115533-44-3
ethyl O-<4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: HBF₄ / dimethylformamide; diethyl ether / 4 h / Ambient temperature

2: 1.) sodium hydride / 1.) N,N-dimethylformamide, r.t., 45 min, 2.) 50 deg C, 4 h

3: 86 percent / NaBH₃CN, molecular sieves 3 Angstroem, HCl / tetrahydrofuran; diethyl ether / 0 °C

4: 94 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂; toluene / 45 h / -45 °C

5: K₂CO₃ / methanol / 4 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether

With hydrogenchloride; tetrafluoroboric acid; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0008-6215(00)90561-5