{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

Base Information

Chemical Name:{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester
CAS No.:220567-88-4
Molecular Formula:C₂₅H₃₆O₈
Molecular Weight:464.556
Hs Code.:

Synonyms:{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

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Chemical Property of {(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

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Technology Process of {(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

There total 6 articles about {(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester 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:

: 99603-55-1
(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

: 220567-88-4
{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / SnCl₄ / CH₂Cl₂ / 15 h / -78 °C

2: 80 percent / HF*pyridine / pyridine / 0.17 h / 0 °C

3: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

4: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

With (+/-)-camphor sulfonic acid; tin(IV) chloride; pyridine hydrogenfluoride; lithium diisopropyl amide; In pyridine; dichloromethane;
DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 220567-88-4
{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

With (+/-)-camphor sulfonic acid; lithium diisopropyl amide; In dichloromethane;
DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 220567-88-4
{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1.) Et₂O, room temperature, 30 min, 2.) 0 deg C to room temperature, 4 h

2: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

3: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

With (+/-)-camphor sulfonic acid; sodium hydride; lithium diisopropyl amide; In dichloromethane;
DOI:10.1016/S0040-4020(98)01206-X