(E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol

Base Information

• Chemical Name: (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol
• CAS No.: 476452-80-9
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:(E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol

Chemical Property of (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol

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Technology Process of (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol

There total 3 articles about (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-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:

tert-Butyl-{(E)-4-(4-methoxy-benzyloxy)-1-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-enyloxy}-dimethyl-silane → (E)-(S)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol + (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol (476452-80-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1021/ja0533646

Reference yield:

(E)-(2R,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,7-bis-(4-methoxy-benzyloxy)-hept-5-ene-2,3-diol → (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol (476452-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 1.75 h / 0 °C

2: TBAF / tetrahydrofuran / 16 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0533646

Reference yield:

1,1-dimethoxycyclopentane (931-94-2) → (E)-(R)-4-(4-Methoxy-benzyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-but-2-en-1-ol (476452-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 1.75 h / 0 °C

2: TBAF / tetrahydrofuran / 16 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0533646

upstream raw materials:

1,1-dimethoxycyclopentane

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