(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Base Information

Chemical Name:(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol
CAS No.:344315-43-1
Molecular Formula:C₃₅H₄₂O₆S₂
Molecular Weight:622.847
Hs Code.:

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Synonyms:(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

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Chemical Property of (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

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Technology Process of (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

There total 40 articles about (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol 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: 94.0%

: 344315-36-2
(2S,3S,4R,4aR,5aR,8R,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

: 344315-43-1
(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: (2S,3S,4R,4aR,5aR,8R,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol; With triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In toluene;

With potassium carbonate; In methanol;
DOI:10.1016/S0040-4039(01)00286-6

Reference yield:

: 4-Nitro-benzoic acid (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

: 344315-43-1
(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

: 344315-31-7
2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol

: 344315-43-1
(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / O₂; CuCl; PdCl₂ / dimethylformamide; H₂O / 48 h / 20 °C

2: Jones' reagent / acetone / 0.5 h / 0 °C

3: I(collidine)2PF₆ / CH₂Cl₂ / 2 h / 20 °C

4: 392 mg / Zn(OTf)2 / CH₂Cl₂ / 2 h / 20 °C

5: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

6: 64.0 mg / DBU / tetrahydrofuran / 3 h / 20 °C

7: 27.5 mg / K₂CO₃ / methanol / 9 h / 20 °C

8: 80 percent / BF₃*OEt₂ / CH₂Cl₂; 1,2-dichloro-ethane / 0.5 h / 20 °C

9: Ph₃P; diethyl azodicarboxylate / toluene / 0.67 h / 20 °C

10: 18.7 mg / K₂CO₃ / methanol / 0.5 h / 20 °C

With jones' reagent; boron trifluoride diethyl etherate; oxygen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; copper(l) chloride; palladium dichloride; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; 1: Wacker oxidation;
DOI:10.1016/S0040-4020(02)00044-3