(1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate

Base Information

• Chemical Name: (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate
• CAS No.: 153896-20-9
• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.439
• Mol file: 153896-20-9.mol

Synonyms:(1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate

Chemical Property of (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate

There total 9 articles about (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate 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: 87.0%

benzoic acid (65-85-0,8013-63-6) + Benzoic acid (E)-(R)-1-((2S,3S)-3-hydroxymethyl-oxiranylmethyl)-3-methoxycarbonyl-allyl ester → (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate (153896-20-9)

Guidance literature:

With titanium(IV) isopropylate; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/jo9619241

Reference yield:

{(2S,3S)-3-[(E)-4-(Tetrahydro-pyran-2-yloxy)-but-2-enyl]-oxiranyl}-methanol (153896-17-4) → (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate (153896-20-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

2: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

3: 88 percent / NaH / benzene / 0.5 h / 0 °C

4: 95 percent / conc. HCl / methanol / 0.08 h

5: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

6: 87 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; diethyl (2R,3R)-tartrate; sodium hydride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;

DOI:10.1021/jo9619241

Reference yield:

(E)-7-(Tetrahydro-pyran-2-yloxy)-hept-5-en-2-yn-1-ol (153896-15-2) → (1R)-1-[(2R,3S)-2-(benzoyloxy)-3,4-dihydroxybutyl]-3-(methoxycarbonyl)-2(E)-allyl benzoate (153896-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

2: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

3: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

4: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: 88 percent / NaH / benzene / 0.5 h / 0 °C

6: 95 percent / conc. HCl / methanol / 0.08 h

7: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

8: 87 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; sodium hydride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;

DOI:10.1021/jo9619241

upstream raw materials:

benzoic acid

(E)-7-(Tetrahydro-pyran-2-yloxy)-hept-5-en-2-yn-1-ol

{(2S,3S)-3-[(E)-4-(Tetrahydro-pyran-2-yloxy)-but-2-enyl]-oxiranyl}-methanol

Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester