(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester
• CAS No.: 880883-37-4
• Molecular Formula: C₇₀H₇₇IO₁₅
• Molecular Weight: 1285.28

Synonyms:(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester

Chemical Property of (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Technology Process of (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester

There total 19 articles about (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-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: 73.0%

ethyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-2-octulopyranosid)onate (880883-34-1) + ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate (880883-31-8) → (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester (880883-37-4) + (2R,3R,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -50 - -20 ℃;

DOI:10.1002/anie.200503299

Reference yield:

2,3-di-O-benzyl-4,6-O-benzylidene-D-mannitol → (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester (880883-37-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

2.1: aq. NaOH; tetrabutylammonium sulfate / tetrahydrofuran / 24 h / 20 °C

3.1: 321 mg / camphorsulfonic acid / methanol; tetrahydrofuran / 6 h / 20 °C

4.1: 82 percent / imidazole; Ph₃P; I₂ / 0.25 h / 20 °C

5.1: NaH; tert-BuOH / dimethylformamide / 0 °C

5.2: dimethylformamide / 1 h / 20 °C

6.1: 545 mg / CSA / methanol / 12 h / 0 °C

7.1: 3 Angstroem molecular sieves; dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / 0 °C

7.2: 34 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 73 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -50 - -20 °C

With pyridine; 1H-imidazole; sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; iodine; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; tetrabutylammonium sulfate; triphenylphosphine; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503299

Reference yield:

2,3,5-tri-O-benzyl-4,6-O-benzylidene-D-mannitol → (2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-2-[(R)-2-benzyloxy-2-((2R,3R,4R,6R)-3,4-bis-benzyloxy-6-ethoxycarbonyl-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-3-iodo-tetrahydro-pyran-2-carboxylic acid ethyl ester (880883-37-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / imidazole; Ph₃P; I₂ / 0.25 h / 20 °C

2.1: NaH; tert-BuOH / dimethylformamide / 0 °C

2.2: dimethylformamide / 1 h / 20 °C

3.1: 545 mg / CSA / methanol / 12 h / 0 °C

4.1: 3 Angstroem molecular sieves; dimethyl(methylthio)sulfonium trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / 0 °C

4.2: 34 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 73 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -50 - -20 °C

With 1H-imidazole; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; iodine; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triphenylphosphine; tert-butyl alcohol; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503299

upstream raw materials:

ethyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-2-octulopyranosid)onate

ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

2,3,5-tri-O-benzyl-4,6-O-benzylidene-1-deoxy-1-iodo-D-mannitol

ethyl 4,5,7-tri-O-benzyl-3-deoxy-D-manno-2-octonate 1,3-propylene dithioketal

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