Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 306726-24-9
• Molecular Formula: C₄₅H₅₆O₁₀SeSi
• Molecular Weight: 863.979

Synonyms:Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester

There total 7 articles about Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl 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:

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane (256341-86-3) + Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester → Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester (306726-24-9)

Guidance literature:

With tin(ll) chloride; In diethyl ether; at 0 - 25 ℃; for 3h;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester (306726-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

2: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

3: SnCl₂ / diethyl ether / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Etherification / 2: Rearrangement / 3: Glycosidation;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

(3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-98-7) → Benzoic acid (2R,3R,4R,5S)-3-benzyloxy-5-[(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-4-yl ester (306726-24-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 95 percent / nBu₄NI / dimethylformamide / 2 h / 0 - 25 °C

2.1: 96 percent / PPTS; MeOH / 1 h / 25 °C

3.1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

4.1: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

5.1: SnCl₂ / diethyl ether / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; methanol; pyridinium p-toluenesulfonate; sodium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Etherification / 2.1: Ring cleavage / 3.1: Etherification / 4.1: Rearrangement / 5.1: Glycosidation;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

t-butyldimethylsiyl triflate

phenyl 1-seleno-β-D-xylopyranoside

(3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Downstream raw materials:

C₃₂H₄₆O₉Si

C₂₇H₃₄O₁₁S

C₂₆H₃₂O₉

C₂₆H₃₀O₈

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