tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Base Information

Chemical Name:tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
CAS No.:191935-35-0
Molecular Formula:C₄₁H₅₈O₁₂
Molecular Weight:742.904
Hs Code.:

Synonyms:tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

There total 36 articles about tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 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: 40.0%

: 71432-55-8
2-tert-butyl-1,3-diisopropylisourea

: 191935-34-9
5-ethyl 3,4-dimethyl [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

: 191935-35-0
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: 5-ethyl 3,4-dimethyl [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate; With potassium hydroxide; In 1,4-dioxane; water; at 100 ℃; for 24h;

2-tert-butyl-1,3-diisopropylisourea; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 81801-09-4
4-O-benzyl-2,3-O-isopropylidene-D-threose

: 191935-35-0
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 16 steps

1: 1) NaClO₂, NaH₂PO₄, 2-methyl-2-butene, 2) (COCl)2, DMF / 1) tBuOH, H₂O, 2) CH₂Cl₂

2: nBu₄NI / CH₂Cl₂ / 0 °C

3: LiHMDS / tetrahydrofuran / -78 °C

4: Sn(OTf)2, propionitrile / 1.5 h / -70 °C

5: 82 percent / Hg(OCOCF₃)2 / 4 h / Heating

6: H₂ / 10percent Pd/C / methanol / 17 h

7: 1) Dess-Martin periodinane, 2) NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 1) CH₂Cl₂, 1.5 h, 2) tBuOH, H₂O, 5 h

8: diethyl ether / 0.17 h / 0 °C

9: 88 percent / TMSCl, NaI / acetonitrile / 1 h / 0 °C

10: 2) 10percent aq. HCl / 1) 90 deg C, 2 h, 2) Et₂O, 1.5 h

11: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

12: 1) nBuLi, 2) Dess-Martin periodinane / 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, 10 h

13: 87 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.17 h

14: 68 percent / 90percent aq. TFA / 15 h

15: 1 N KOH / dioxane / 24 h / Heating

16: CH₂Cl₂ / 24 h

With hydrogenchloride; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; N,N-dimethyl-formamide; trifluoroacetic acid; propiononitrile; sodium iodide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1055/s-1997-6154

Reference yield:

: (4S,5R)-4-[(R)-((4R,5S)-2,2-Diethyl-5-methoxymethoxymethyl-[1,3]dioxolan-4-yl)-ethoxycarbonyl-hydroxy-methyl]-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

: 191935-35-0
tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 1) Dess-Martin periodinane, 2) NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 1) CH₂Cl₂, 1.5 h, 2) tBuOH, H₂O, 5 h

2: diethyl ether / 0.17 h / 0 °C

3: 88 percent / TMSCl, NaI / acetonitrile / 1 h / 0 °C

4: 2) 10percent aq. HCl / 1) 90 deg C, 2 h, 2) Et₂O, 1.5 h

5: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

6: 1) nBuLi, 2) Dess-Martin periodinane / 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, 10 h

7: 87 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.17 h

8: 68 percent / 90percent aq. TFA / 15 h

9: 1 N KOH / dioxane / 24 h / Heating

10: CH₂Cl₂ / 24 h

With hydrogenchloride; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; hydrogen; Dess-Martin periodane; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In 1,4-dioxane; diethyl ether; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1055/s-1997-6154