3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Base Information

Chemical Name:3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester
CAS No.:740840-68-0
Molecular Formula:C₈₅H₉₀O₁₄
Molecular Weight:1335.64
Hs Code.:

3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Synonyms:3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

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Chemical Property of 3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

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Technology Process of 3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

There total 5 articles about 3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl 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: 88.0%

: 102208-53-7
(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

: 740840-66-8
(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

: 740840-68-0
3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1002/anie.200353478

Reference yield:

: 232603-06-4
ethyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate

: 740840-68-0
3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / TMSOTf / acetonitrile / 8 h / 0 °C

2: 87 percent / OsO₄; aq. NaIO₄ / tetrahydrofuran / 1.5 h / 20 °C

3: 95 percent / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 6 h / 20 °C

4: 716 mg / aq. LiOH / tetrahydrofuran / 0 - 20 °C

5: 88 percent / 4-DMAP; DCC / CH₂Cl₂

With dmap; lithium hydroxide; sodium chlorite; sodium periodate; dipotassium hydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1002/anie.200353478

Reference yield:

: 740840-62-4
ethyl ((1R)-2,3,4-tri-O-benzyl-1-ethanal-1,6,7-trideoxy-α-D-gluco-octopyranosiduronate)

: 740840-68-0
3-[(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxycarbonylmethyl)-tetrahydro-pyran-2-yl]-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 6 h / 20 °C

2: 716 mg / aq. LiOH / tetrahydrofuran / 0 - 20 °C

3: 88 percent / 4-DMAP; DCC / CH₂Cl₂

With dmap; lithium hydroxide; sodium chlorite; dipotassium hydrogenphosphate; 2-methyl-but-2-ene; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1002/anie.200353478