All Exams Test series for 1 year @ ₹349 only
Question

The major product formed in the following reaction is

2,3-Anhydro methyl pyranoside with a TBDMS-protected CH2OH treated with a cyanocuprate then TBAF

This question was previously asked in
MH SET 2026 Paper 1 Question Paper (25-Oct-2026)
The correct answer is
Pyranoside with methyl, hydroxyl and CH2OH groups

Epoxides fused to a pyranose ring are opened by nucleophiles in an SN2 fashion with trans-diaxial geometry (Fürst–Plattner rule), and the regioselectivity in 2,3-anhydro sugars is strongly biased: attack at C-2, next to the anomeric carbon, is disfavoured because the electronegative ring oxygen and the anomeric OCH3 destabilise the SN2 transition state there.

Step 1 — The higher-order cyanocuprate Me2Cu(CN)Li2 delivers a methyl group to C-3, anti to the epoxide oxygen. The methyl ends up on the face opposite to the former epoxide (hashed), and the oxygen stays on C-2 as a free hydroxyl (wedged), trans to the new methyl.

Step 2 — TBAF cleaves the TBDMS ether and frees the primary CH2OH.

Structures that keep the CH2OTBDMS group overlook the fluoride deprotection, and those with the methyl at C-2 and the hydroxyl at C-3 correspond to the disfavoured attack next to the anomeric centre.

the 3-C-methyl pyranoside with a free 2-OH and CH2OH group option is correct.

Was this answer helpful?

Similar Questions

  1. The hybridization for the complex ion [FeF6]3- and [Fe(CN)6]3- is :

  2. Which of the following diatomic molecules is paramagnetic ?

  3. Size of the d orbitals for Si, P, S and Cl follow the order :

  4. The molecules P4 and CH4 exhibit the same :

  5. The bond order for O2 and the hypothetical molecules N2- and O2+ will follow the trend :

  6. According to CFT, Ni2+ can have two unpaired electrons in :

  7. Which of the following complexes will NOT exhibit ideal octahedral geometry ?

  8. The carbonyl stretching frequency (νCO) for the complexes (i) [Co(CO)4]- (ii) [Ni(CO)4] and (iii) [Fe(CO)4]2- will follow the trend :

  9. The spin only magnetic moment for the complex Hg[Co(SCN)4] is :

  10. The molecular formula for sodium bis (thiosulphato) argentate (I) is :


Important Questions from Mixed Topic (MH-SET)

  1. .................... is a client server application that identifies each host on the internet with a unique user-friendly name.

  2. Every OS has a ................ or .......... which primarily resides in the main memory of the computer to perform some of the basic functions of the OS.

    (i) Kernel

    (ii) Interface

    (iii) Nucleus

    (iv) Compiler

    Codes:

  3. Which of the following are referred to as low level language?

    (i) Machine language

    (ii) Assembly language

    (iii) High level language

    (iv) Natural language

    Codes:

  4. Match the following:

    List IList II
    (a) New York Public Library(i) Shelv AR
    (b) Miami University Augmented Research Group(ii) Smart library
    (c) Oula University Library(iii) Wolf Walk
    (d) North Carolina State University(iv) Find the future

    Codes:

  5. Which part of the QR code represents the encoded data?

Need Expert Advice?
Upcoming Exams
CTET
December 12, 2026
CBSE UGC NET
December 14, 2026
CSIR UGC NET
December 19, 2026
Test Series
MH-SET img
Teaching
MAHA TAIT Mock Test Series (New)
58 Tests 1 Tests Free
3854 Attempts
4.9(108)
English, Hindi, Marathi
More Questions from MH-SET

Start Your Preparation with Prepp Mobile App

Download the app from Google Play & App Store
Download the app from Google Play & App Store
Prepp Mobile App