(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

Base Information

Chemical Name:(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one
CAS No.:78442-78-1
Molecular Formula:C₄₁H₅₈O₈S₃
Molecular Weight:775.105
Hs Code.:

(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

Synonyms:(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

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Chemical Property of (R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

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Technology Process of (R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

There total 23 articles about (R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one 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:

: (4R,6S,8aR)-6-(2-Benzyloxy-ethyl)-3,4,6,8a-tetrahydro-2H,7H-thiopyrano[2,3-b]thiopyran-4-ol

: 78442-78-1
(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 11 steps

1: KH / tetrahydrofuran / 0 °C

2: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

3: TsOH / CH₂Cl₂ / 0 °C

4: EtOH / Ra(Ni)-(W-2) / Heating

6: 1.) mesityllithium, 2.) (CF₃CO)2O, Me₂SO, 3.) (i-Pt)2NEt

7: 1.) KH / 1.) HMPA, THF, 0 deg C -> -78 deg C, 2.) -78 deg C

8: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

9: pyridine / 0 °C

10: DMAP, pyridine / methanol / 30 °C

11: b-BuLi / tetrahydrofuran / -50 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; ethanol; mesityllithium; potassium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; nickel; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00401a049

Reference yield:

: 78442-72-5
(6S,8aR)-6-(2-Benzyloxy-ethyl)-2,3,6,8a-tetrahydro-7H-thiopyrano[2,3-b]thiopyran-4-one

: 78442-78-1
(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 12 steps

1: NaBH₄ / methanol / 0 °C

2: KH / tetrahydrofuran / 0 °C

3: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

4: TsOH / CH₂Cl₂ / 0 °C

5: EtOH / Ra(Ni)-(W-2) / Heating

7: 1.) mesityllithium, 2.) (CF₃CO)2O, Me₂SO, 3.) (i-Pt)2NEt

8: 1.) KH / 1.) HMPA, THF, 0 deg C -> -78 deg C, 2.) -78 deg C

9: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

10: pyridine / 0 °C

11: DMAP, pyridine / methanol / 30 °C

12: b-BuLi / tetrahydrofuran / -50 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; ethanol; mesityllithium; potassium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; nickel; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00401a049

Reference yield:

: 78442-70-3
4-Benzyloxy-2-((R)-4-oxo-tetrahydro-thiopyran-2-ylsulfanylmethyl)-butyraldehyde

: 78442-78-1
(R)-1-[(3aR,4S,6aS,9R,10aS)-4-(2-Benzyloxy-ethyl)-10-benzylsulfanyl-2,2-dimethyl-tetrahydro-1,3-dioxa-6,7-dithia-cyclopenta[d]naphthalen-9-yl]-2-[(4R,5R)-5-((R)-1-methoxymethoxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 15 steps

1: SiO₂

2: pyridine / Ambient temperature

3: alumina / ethyl acetate / Ambient temperature

4: NaBH₄ / methanol / 0 °C

5: KH / tetrahydrofuran / 0 °C

6: 1.) OsO₄, 2.) NaHSO₃ / 1.) Et₂O, room temperature, 2.) aq. pyridine, room temperature

7: TsOH / CH₂Cl₂ / 0 °C

8: EtOH / Ra(Ni)-(W-2) / Heating

10: 1.) mesityllithium, 2.) (CF₃CO)2O, Me₂SO, 3.) (i-Pt)2NEt

11: 1.) KH / 1.) HMPA, THF, 0 deg C -> -78 deg C, 2.) -78 deg C

12: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

13: pyridine / 0 °C

14: DMAP, pyridine / methanol / 30 °C

15: b-BuLi / tetrahydrofuran / -50 °C

With pyridine; dmap; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; ethanol; mesityllithium; silica gel; potassium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; nickel; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/ja00401a049