5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

Chemical Name:5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
CAS No.:522633-06-3
Molecular Formula:C₅₂H₅₈O₁₂S
Molecular Weight:907.091
Hs Code.:

5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Synonyms:5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Chemical Property of 5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Technology Process of 5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 7 articles about 5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 65.0%

: 522633-05-2
5-[(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 522633-06-3
5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: With hydrazinium monoacetate; In methanol; dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 118-90-1
ortho-methylbenzoic acid

: 522633-06-3
5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / HBr; o-phosphoric acid / acetic acid / 3 h / 115 °C

2: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

3: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

4: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

5: 90 percent / TFA / CH₂Cl₂ / 4 h

6: 75 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

7: 65 percent / hydrazinium acetate / CH₂Cl₂; methanol / 2 h / 20 °C

With dmap; phosphoric acid; boron trifluoride diethyl etherate; hydrogen bromide; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; cyclohexane; acetic acid; toluene;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

: 72985-19-4
5-(bromomethyl)-2-methylbenzoic acid

: 522633-06-3
5-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-2-methyl-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 20 °C

2: 70 percent / Bu₂SnO; TBAI / toluene / 11 h / Heating

3: 75 percent / DCC; DMAP / CH₂Cl₂ / 24 h

4: 90 percent / TFA / CH₂Cl₂ / 4 h

5: 75 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

6: 65 percent / hydrazinium acetate / CH₂Cl₂; methanol / 2 h / 20 °C

With dmap; boron trifluoride diethyl etherate; hydrazinium monoacetate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; cyclohexane; toluene;
DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S