(3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole
• CAS No.: 96212-56-5
• Molecular Formula: C₄₀H₄₂O₆
• Molecular Weight: 618.77

Synonyms:(3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

There total 15 articles about (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole 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: 55.0%

Methanesulfonic acid (3aR,4aR,5R,8R,8aR,8bR)-8a-benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-7-yl ester → (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (96212-56-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium acetate; at 100 ℃; for 96h;

DOI:10.1021/jo00209a050

Reference yield:

(3aR,5R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (39838-77-2,51996-47-5) → (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (96212-56-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 76 percent / NaH, Bu₄N⁺Br^-

2: 95 percent / H₃O⁺

3: 98 percent / Et₃N

4: 98 percent / NaH, Bu₄N⁺I^-

5: 98 percent / Bu₄N⁺F^-

6: 90 percent / (COCl)2, Me₂SO, Et₃N

7: 1.) t-BuOK, 2.) MsCl

8: 60 percent

9: 74 percent / PhNCO, Et₃N / benzene / Heating

10: 67 percent / H₂ / Ni

11: 65 percent / LiAlH₄

12: 90 percent

13: 86 percent

14: 55 percent / NaOAc, HMPA / 96 h / 100 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; oxalyl dichloride; oxonium; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; phenyl isocyanate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; nickel; In benzene;

DOI:10.1021/jo00209a050

Reference yield:

benzyl bromide (100-39-0) → (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (96212-56-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 76 percent / NaH, Bu₄N⁺Br^-

2: 95 percent / H₃O⁺

3: 98 percent / Et₃N

4: 98 percent / NaH, Bu₄N⁺I^-

5: 98 percent / Bu₄N⁺F^-

6: 90 percent / (COCl)2, Me₂SO, Et₃N

7: 1.) t-BuOK, 2.) MsCl

8: 60 percent

9: 74 percent / PhNCO, Et₃N / benzene / Heating

10: 67 percent / H₂ / Ni

11: 65 percent / LiAlH₄

12: 90 percent

13: 86 percent

14: 55 percent / NaOAc, HMPA / 96 h / 100 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; oxalyl dichloride; oxonium; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; phenyl isocyanate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; nickel; In benzene;

DOI:10.1021/jo00209a050

upstream raw materials:

(3aR,5R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

benzyl bromide

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(R)-2-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methoxy-ethanol

Downstream raw materials:

((3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-8-yl)-methanol

2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

2,2-Dimethyl-propionic acid (1S,4R,5R,6S)-6-benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-5-hydroxy-4-methoxy-3-methyl-cyclohex-2-enylmethyl ester

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