(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran
CAS No.:232603-16-6
Molecular Formula:C₅₈H₆₄O₉
Molecular Weight:905.141
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

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Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

There total 7 articles about (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran 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: 71.0%

: 232603-12-2
3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate

: 74-95-3
1,1-dibromomethane

: 232603-16-6
(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc;
DOI:10.1016/S0040-4039(99)00815-1

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 232603-16-6
(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: Swern reagent / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -78 °C

2: 85 percent / benzene / 4 h / 20 °C

3: 95 percent / H₂ / Lindlar catalyst / ethyl acetate / 12 h / 20 °C / 1810.07 Torr

4: 97 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

5: 94 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

6: 71 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 0.75 h / 60 °C

With dmap; lithium hydroxide; swern reagent; N,N,N,N,-tetramethylethylenediamine; hydrogen; titanium tetrachloride; dicyclohexyl-carbodiimide; zinc; Lindlar's catalyst; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; benzene; 1: Swern oxidation / 2: Wittig reaction / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: Esterification / 6: methylenation;
DOI:10.1021/jo0005159

Reference yield:

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

: 232603-16-6
(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[3-((1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-but-3-enyl]-6-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

2: 94 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

3: 71 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 0.75 h / 60 °C

With dmap; lithium hydroxide; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; dicyclohexyl-carbodiimide; zinc; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; 1: Hydrolysis / 2: Esterification / 3: methylenation;
DOI:10.1021/jo0005159