((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

Base Information

Chemical Name:((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate
CAS No.:943032-41-5
Molecular Formula:C₂₇H₃₄O₆
Molecular Weight:454.563
Hs Code.:

Synonyms:((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

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Chemical Property of ((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

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Technology Process of ((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

There total 6 articles about ((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate 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: 99.0%

: 100-44-7
benzyl chloride

: 827043-47-0
(1R,2R,3S)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

: 943032-41-5
((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

Guidance literature:: With pyridine; dmap; at 20 ℃; for 4h;
DOI:10.1248/cpb.54.1459

Reference yield:

: 138-59-0
shikimic acid

: 943032-41-5
((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / SOCl₂ / 10 °C

2: 90 percent / (+/-)-CSA / methanol / 48 h / 90 °C

3: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 5 h / 20 °C

4: 10.8 g / CH₃ONa / methanol / 2 h / 20 °C

5: 90 percent / diisobutylaluminum hydride / toluene / -78 °C

6: 99 percent / DMAP; pyridine / 4 h / 20 °C

With pyridine; dmap; thionyl chloride; 10-camphorsufonic acid; sodium methylate; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 3: Mitsunobu reaction;
DOI:10.1248/cpb.54.1459

Reference yield:

: 40983-58-2
methyl shikimate

: 943032-41-5
((2S,3S,4aR,8S,8aR)-8-(benzyloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-6-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / (+/-)-CSA / methanol / 48 h / 90 °C

2: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 5 h / 20 °C

3: 10.8 g / CH₃ONa / methanol / 2 h / 20 °C

4: 90 percent / diisobutylaluminum hydride / toluene / -78 °C

5: 99 percent / DMAP; pyridine / 4 h / 20 °C

With pyridine; dmap; 10-camphorsufonic acid; sodium methylate; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 2: Mitsunobu reaction;
DOI:10.1248/cpb.54.1459