(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

Base Information

Chemical Name:(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one
CAS No.:482646-93-5
Molecular Formula:C₅₄H₅₈O₁₀
Molecular Weight:867.049
Hs Code.:

(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

Synonyms:(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

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Chemical Property of (2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

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Technology Process of (2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

There total 4 articles about (2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-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: 100.0%

: 482647-17-6
(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

: 482646-93-5
(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

Guidance literature:: With sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1055/s-2002-34904

Reference yield:

: 482647-16-5
(2S,3R,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-2,3,5a,7,8,10a-hexahydro-1,6-dioxa-heptalen-3-ol

: 482646-93-5
(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

2: 100 percent / DDQ; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

With oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; 1: Swern oxidation;
DOI:10.1055/s-2002-34904

Reference yield:

: 482647-15-4
(2S,3R,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-hydroxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-2,3,5a,7,8,10a-hexahydro-1,6-dioxa-heptalen-3-ol

: 482646-93-5
(2S,5aS,7R,8S,10aR)-8-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-5a,7,8,10a-tetrahydro-1,6-dioxa-heptalen-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / K₂CO₃ / dimethylformamide / 14 h / 55 °C

2: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

3: 100 percent / DDQ; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

With oxalyl dichloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; 2: Swern oxidation;
DOI:10.1055/s-2002-34904