((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Base Information

Chemical Name:((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester
CAS No.:557088-10-5
Molecular Formula:C₅₇H₆₂O₁₀
Molecular Weight:907.113
Hs Code.:

((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Synonyms:((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

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Chemical Property of ((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

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Technology Process of ((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

There total 7 articles about ((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic 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: 77.0%

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

: 557087-96-4
((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid

: 557088-10-5
((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/jo030039x

Reference yield:

: 100-39-0
benzyl bromide

: 557088-10-5
((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / methanol / 2 h / 20 °C

1.2: NaH / dimethylformamide / 12 h / 23 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 69 percent / Zn; AcOH / CH₂Cl₂ / -78 - 20 °C

3.1: 87 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

4.1: 77 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium hydride; ozone; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo030039x

Reference yield:

: 118354-00-0
methyl 2,4,6-tri-O-acetyl-α-D-galactopyranoside

: 557088-10-5
((2R,3R,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / pyridine; DMAP; NHS / toluene / 1 h / 70 °C

2.1: 64 percent / AIBN / benzene / 1.5 h / Heating

3.1: NaH / methanol / 2 h / 20 °C

3.2: NaH / dimethylformamide / 12 h / 23 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 69 percent / Zn; AcOH / CH₂Cl₂ / -78 - 20 °C

5.1: 87 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

6.1: 77 percent / 4-DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 1-hydroxy-pyrrolidine-2,5-dione; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); sodium hydride; ozone; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jo030039x